Category: 15799-79-8

Related Products of 15799-79-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15799-79-8 name is 3-Methoxy-N,N-dimethylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[0147] (S)-3-(4-Dimethylamino-2-methoxy-phenyl)-3-phenyl-propanol: To a 50-mL roundbottom flask equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (0.394 g, 1.60 mmol, 0.100 equiv), CH2Cl2 (16.0 mL), HCl (as a 4N solution in 1,4-dioxane, 0.400 mL, 1.60 mmol, 0.100 equiv), and N,N-dimethyl-m-anisidine (4.69 mL, 32.0 mmol, 2.00 equiv). The reaction vessel was cooled to 0o C. before the addition of cinnamaldehyde (2.06 ml, 16.0 mmol, 1.00 equiv). The solution was stirred for 12 h at 0o C. and then warmed to ambient temperature and stirred for an additional 6 h. At that time, the reaction mixture was added drop-wise to a stirring suspension of NaBH4 (0.750 g, 0.198 mmol, 1.24 equiv) in ethanol. After 5 min, the reduction was quenched with saturated aqueous NaHCO3 solution and diluted with CH2Cl2. The layers were separated and the organic was washed with saturated aqueous NaHCO3 and brine solutions. The resulting solution was dried over sodium sulfate and concentrated in vacuo to give a pale yellow residue, which was purified by silica gel chromatography. Gradient elution with 25-50% EtOAc in hexanes afforded the product as a colorless oil in 81% yield (3.70 g, 13.0 mmol); 74% ee. 1H NMR (300 MHz, CDCl3) ?7.32-7.12 (m, 5H, ArH), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.31 (dd, J=2.7, 8.8 Hz, 1H, ArH), 6.27 (d, J=2.2, Hz, 1H, ArH), 4.51 (dd, J=6.6, 8.8 Hz, 1H, ArCH), 3.83 (s, 3H, OCH3), 3.65-3.48 (m, 2H, CH2OH), 2.93 (s, 6H, N(CH3)2), 2.38-2.12 (m, 2H, CHCH2), 1.98 (br s, 1H, OH); 13C NMR (75 MHz, CDCl3) ?157.8, 150.5, 145.5, 128.8, 128.4, 128.2, 125.9, 121.3, 105.5, 96.6, 61.6, 55.9, 41.1, 38.7, 38.2. [0148] The enantiomeric ratio of the product was determined by HPLC analysis using a Chiracel AD and AD guard column (10% ethanol/hexanes, 1 mL/min); R isomer tr=12.9 min, S isomer tr=18.1 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-N,N-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 15799-79-8, Formula: C9H13NO

[0086] (R)-3-(4-Dimethylamino-2-methoxy-phenyl)-butyraldehyde (Table 1, entry 1). To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (12.3 mg, 0.050 mmol, 0.100 equiv), CH2Cl2 (0.50 ml), HCl (as a 4N solution in 1,4-dioxane, 12.5 uL, 0.050 mmol, 0.100 equiv), and N,N-dimethyl-m-anisidine (73.3 uL, 0.500 mmol, 1.00 equiv). The solution was cooled to -40o C. before crotonaldehyde (124 uL, 1.50 mmol, 3.00 equiv) was added. After 36 h, the reaction mixture was subjected directly to silica gel chromatography. Elution with 20% EtOAc in hexanes followed by concentration and removal of residual crotonaldehyde under vacuum afforded the product as a colorless oil in 86% yield (94.9 mg, 0.429 mmol); 89% ee. IR (film) 2958, 2874, 2834, 2719, 1721, 1615, 1568, 1516, 1462, 1441, 1352, 1238, 1133, 1034, 979.6, 814.0 cm-1; 1H NMR (300 MHz, CDCl3) ?9.67 (t, J=2.7 Hz, 1H, CHO), 7.03 (d, J=8.2 Hz, 1H, ArH), 6.31 (dd, J=2.5, 8.2 Hz, 1H, ArH), 6.27 (d, J=2.5 Hz, 1H, ArH), 3.83 (s, 3H, OCH3), 3.63 (dq, J=7.1, 7.1 Hz, 1H, ArCH), 2.94 (s, 6H, N(CH3)2), 2.68 (ddd, J=2.5, 6.9, 15.9 Hz, 1H, CH2CO), 2.55 (ddd, J=2.8, 7.7, 15.9 Hz, 1H, CH2CO), 1.27 (d, 3H, CHCH3); 13C NMR (75 MHz, CDCl3) ?203.7, 157.8, 150.9, 127.5, 121.7, 15.1, 96.6, 55.4, 51.2, 41.0, 27.6, 20.9. HRMS (CI) exact mass calcd for (C13H19NO2) requires m/z 222.1494 for [M+H]+, found m/z 222.1497. [?]D=-9.5 (c=1.0, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (3.0% ethanol/hexanes, 1 mL/min); S isomer tr=21.6 min, R isomer tr=23.1 min.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 15799-79-8, These common heterocyclic compound, 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[0134] (R)-4-Oxo-2-(4-dimethylamino-2-methoxyphenyl)-butyric acid methyl ester (Table 2, entries 11 & 12): To an amber 2-dram vial equipped with a magnetic stir bar was added (2S, 5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (6.13 mg, 0.0250 mmol, 0.100 equiv), 4-methyl ester (28.5 mg, 0.250 mmol, 1.00 equiv), CHCl3 (0.25 ml), HCl (as a 4N solution in 1,4-dioxane, 6.25 uL, 0.0250 mmol, 0.100 equiv), and 3-dimethylamino-anisole (44 uL, 0.30 mmol, 1.2 equiv). The solution was stirred for 5 min at ambient temperature and subjected directly to silica gel chromatography. Gradient elution with 20-40% EtOAc in hexanes afforded the product as a colorless oil in 73% yield (48.2 mg, 0.182 mmol); 91% ee. IR (film) 2950, 2903, 2838, 2727, 1730, 1616, 1569, 1519, 1462, 1440, 1356, 1242, 1171, 1114, 1033, 979.4, 814.6, 642.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.77 (t, J=1.1 Hz, 1H, CHO), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.27 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.22 (d, J=2.5 Hz, 1H, ArH) 4.38 (dd, J=5.2, 9.1 Hz, 1H, ArCH), 3.81 (s, 3H, ArOCH3), 3.66 (s, 3H, CO2CH3), 3.52 (ddd, J=1.4, 9.1, 18.1 Hz, 1H, CH2CO), 2.94 (s, 6H, N(CH3)2), 2.67 (ddd, J=0.8, 4.9, 17.8 Hz, 1H CH2CO); 13C NMR (75 MHz, CDCl3) ?201.0, 174.4, 157.5, 151.5, 129.3, 114.6, 104.9, 96.2, 55.6, 52.5, 46.7, 40.9, 39.2. HRMS (CI) exact mass calcd for (C21H23NO3) requires m/z 266.1392 for [M+H]+, found m/z 266.1387. [?]D=-149.0 (c=1.0, CHCl3). [0135] The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction in ethanol at 0o C.) using a Chiracel AD and AD guard column (6.0% ethanol/hexanes, 1 mL/min); S isomer tr=26.0 min, R isomer tr=27.8 min. The same reaction conducted at -20o C. on 0.5-mmol scale was complete after 8 h and purified in identical fashion to give the product in 90% yield (119 mg, 0.448 mmol) and 92% ee. EXAMPLE 8 [0104] (R)-4-Oxo-2-(4-dimethylamino-2-methoxyphenyl)-butyric acid methyl ester (Table 1, entry 6): To an amber 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (6.13 mg, 0.0250 mmol, 0.100 equiv), CHCl3 (0.25 ml), HCl (as a 4N solution in 1,4-dioxane, 6.25 uL, 0.0250 mmol, 0.100 equiv), and 3-dimethylamino-anisole (44 uL, 0.30 mmol, 1.2 equiv). The solution was cooled to -20o C. before oxobutenoic acid methyl ester (28.5 mg, 0.250 mmol, 1.00 equiv) was added. The resulting solution was maintained at -20o C. for 8 h and then subjected directly silica gel chromatography. Gradient elution with 20-40% EtOAc in hexanes afforded the product as a colorless oil in 73% yield (48.2 mg, 0.182 mmol); 91% ee. IR (film) 2950, 2903, 2838, 2727, 1730, 1616, 1569, 1519, 1462, 1440, 1356, 1242, 1171, 1114, 1033, 979.4, 814.6, 642.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.77 (t, J=1.1 Hz, 1H, CHO), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.27 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.22 (d, J=2.5 Hz, 1H, ArH), 4.38 (dd, J=5.2, 9.1 Hz, 1H, ArCH), 3.81 (s, 3H, ArOCH3), 3.66 (s, 3H, CO2CH3), 3.52 (ddd, J=1.4, 9.1, 18.1 Hz, 1H, CH2CO), 2.94 (s, 6H, N(CH3)2), 2.67 (ddd, J=0.8, 4.9, 17.8 Hz, 1H, CH2CO); 13C NMR (75 MHz, CDCl3) ?201.0, 174.4, 157.5, 151.5, 129.3, 114.6, 104.9, 96.2, 55.6, 52.5, 46.7, 40.9, 39.2. HRMS (CI) exact mass calcd for (C21H23NO3) requires m/z 266.1392 for [M+H]+, found m/z 266.1387. [?]D=-149.0 (c=1.0, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction in ethanol at 0o C.) using a Chiracel AD and AD guard column (6.0% ethanol/hexanes, 1 mL/min); S isomer tr=26.0 min, R isomer tr=27.8 min.

The synthetic route of 15799-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 3-Methoxy-N,N-dimethylaniline

[0092] (R)-3-(4-Dimethylamino-2-methoxy-phenyl)-pentanal (Table 1, entry 3): To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol, 0.200 equiv), CH2Cl2 (0.50 ml), HCl (as a 4N solution in 1,4-dioxane, 25.0 uL, 0.100 mmol, 0.200 equiv), and N,N-dimethyl-m-anisidine (73.3 uL, 0.500 mmol, 1.00 equiv). The solution was cooled to -50o C. before pentenal (98.0 uL, 1.00 mmol, 2.00 equiv) was added. After 62 h, the reaction mixture was subjected directly to silica gel chromatography. Elution with 20% EtOAc in hexanes followed by concentration and removal of residual pentenal under vacuum afforded the product as a colorless oil in 68% yield (79.5 mg, 0.338 mmol); 88% ee. IR (film) 2959, 2926, 2871, 2839, 2800, 2721, 1718, 1616, 1569, 1517, 1351, 1237, 1136, 1034, 979.5, 812.9 cm-1;1H NMR (300 MHz, CDCl3) ?9.63 (t, J=2.8 Hz, 1H, CHO), 6.97 (d, J=8.2 Hz, 1H, ArH), 6.30 (dd, J=2.5, 8.3 Hz, 1H, ArH), 6.26 (d, J=2.5 Hz, 1H, ArH), 3.81 (s, 3H, OCH3), 3.40 (dt, J=7.3, 7.4 Hz, 1H, ArCH), 2.94 (s, 6H, N(CH3)2), 2.66 (dd, J=2.7, 7.4 Hz, 2H, CH2CO), 1.72-1.61 (m, 2H, CH2CH3), 0.83 (t, J=7.4 Hz, 3H, CH2CH3); 13C NMR (75 MHz, CDCl3) 203.8, 158.2, 150.6, 128.4, 119.8, 105.0, 96.5, 55.5, 49.7, 1.1, 34.9, 28.4, 12.4. HRMS (CI) exact mass calcd for (C14H21NO2) requires m/z 236.1650 for [M+H]+, found m/z 236.1649. [?]D=-18.9 (c=0.970, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (3.0% ethanol/hexanes, 1 mL/min); S isomer tr=11.5 min, R isomer tr=12.4 min.

According to the analysis of related databases, 15799-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

[0095] (S)-4-Benzoyloxy-3-(4-dimethylamino-2-methoxy-phenyl)-butyraldehyde (Table 1, entry 4): To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tertbutyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol, 0.100 equiv), N,N-dimethyl-anisidine hydrochloride (18.8 mg, 0.100 mmol., 0.100 equiv), CHCl3 (1.00 ml), and N,N-dimethyl-m-anisidine (132 uL, 0.900 mmol, 0.900 equiv). The solution was cooled to -20o C. before 4-benzoyloxy-crotonaldehyde (0.380, 2.00 mmol, 2.00 equiv) was added as a solid. After 24 h, the reaction mixture was subjected directly to silica gel chromatography. Gradient elution with 10-25% EtOAc in hexanes followed by concentration and removal of residual pentenal under vacuum afforded the product as a colorless oil in 89% yield (304 mg, 0.889 mmol); 92% ee. IR (film) 2940, 2892, 2836, 2724, 1719, 1615, 1518, 1273, 1240, 1117, 712.5 cm-1; 1H NMR (300 MHz, CDCl3) ?9.74 (t, J=2.1 Hz, 1H, CHO), 8.01 (ddd, J=0.6, 1.1, 6.3 Hz., 2H, ArH), 7.58-7.40 (m, 3H, ArH), 7.08 (d, J=8.2 Hz, 1H, ArH), 6.30 (dd, J=2.5, 8.5 Hz, 1H, ArH), 6.25 (d, J=2.4 Hz, 1H, ArH), 4.51 (dd, J=5.5, 10.7 Hz, 1H, CH2O), 4.42 (dd, J=8.2, 10.7 Hz, 1H, CH2O), 4.08-3.98 (m, 1H, ArCH), 3.83 (s, 3H, OCH3), 2.98-2.80 (m, 2H, CH2CO), 2.95 (s, 6H, N(CH3); 13C NMR (75 MHz, CDCl3) 202.2, 166.6, 158.2, 151.3, 133.1, 130.3, 129.8, 129.0, 128.6, 115.6, 104.9, 96.3, 67.9, 55.4, 46.3, 50.0, 33.5. HRMS (CI) exact mass calcd for (C20H23NO4) requires m/z 342.1705 for [M+H]+, found m/z 342.1705. [?]D =-16.9 (c=0.751, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (10% ethanol/hexanes, 1 mL/min); R isomer tr=15.2 min, S isomer tr=24.0 min.

The synthetic route of 15799-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 15799-79-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 15799-79-8 name is 3-Methoxy-N,N-dimethylaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

[0147] (S)-3-(4-Dimethylamino-2-methoxy-phenyl)-3-phenyl-propanol: To a 50-mL roundbottom flask equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (0.394 g, 1.60 mmol, 0.100 equiv), CH2Cl2 (16.0 mL), HCl (as a 4N solution in 1,4-dioxane, 0.400 mL, 1.60 mmol, 0.100 equiv), and N,N-dimethyl-m-anisidine (4.69 mL, 32.0 mmol, 2.00 equiv). The reaction vessel was cooled to 0o C. before the addition of cinnamaldehyde (2.06 ml, 16.0 mmol, 1.00 equiv). The solution was stirred for 12 h at 0o C. and then warmed to ambient temperature and stirred for an additional 6 h. At that time, the reaction mixture was added drop-wise to a stirring suspension of NaBH4 (0.750 g, 0.198 mmol, 1.24 equiv) in ethanol. After 5 min, the reduction was quenched with saturated aqueous NaHCO3 solution and diluted with CH2Cl2. The layers were separated and the organic was washed with saturated aqueous NaHCO3 and brine solutions. The resulting solution was dried over sodium sulfate and concentrated in vacuo to give a pale yellow residue, which was purified by silica gel chromatography. Gradient elution with 25-50% EtOAc in hexanes afforded the product as a colorless oil in 81% yield (3.70 g, 13.0 mmol); 74% ee. 1H NMR (300 MHz, CDCl3) ?7.32-7.12 (m, 5H, ArH), 6.99 (d, J=8.2 Hz, 1H, ArH), 6.31 (dd, J=2.7, 8.8 Hz, 1H, ArH), 6.27 (d, J=2.2, Hz, 1H, ArH), 4.51 (dd, J=6.6, 8.8 Hz, 1H, ArCH), 3.83 (s, 3H, OCH3), 3.65-3.48 (m, 2H, CH2OH), 2.93 (s, 6H, N(CH3)2), 2.38-2.12 (m, 2H, CHCH2), 1.98 (br s, 1H, OH); 13C NMR (75 MHz, CDCl3) ?157.8, 150.5, 145.5, 128.8, 128.4, 128.2, 125.9, 121.3, 105.5, 96.6, 61.6, 55.9, 41.1, 38.7, 38.2. [0148] The enantiomeric ratio of the product was determined by HPLC analysis using a Chiracel AD and AD guard column (10% ethanol/hexanes, 1 mL/min); R isomer tr=12.9 min, S isomer tr=18.1 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methoxy-N,N-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Patent; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 15799-79-8, A common heterocyclic compound, 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, molecular formula is C9H13NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A round-bottom flask was chargedwith N,N-dialkyl aniline dissolved in toluene solution, under N2 condition. TBHP was added drop wise and reaction was stirred for 2 min. Triethylamine was added thereafter, and then the contents of the reaction were stirred for 3 h at 110 C under inert N2 condition. The reaction mixture was washed 2-3 times with H2O and ethyl acetate. The upper organic layer was separated and dried over sodium sulphate and then subjected to rotavapour. The crude mixture was purified by column chromatography on silica gel (60-120).

The synthetic route of 15799-79-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Botla, Vinayak; Barreddi, Chiranjeevi; Daggupati, Ramana V; Malapaka, Chandrasekharam; Journal of Chemical Sciences; vol. 128; 9; (2016); p. 1469 – 1473;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 15799-79-8 as follows. HPLC of Formula: C9H13NO

General procedure: (Scheme 1: cat.= H3PW12O40, oxidant= air, solvent= DMSO/CH3CO2H). A 50mL flask equipped with a magnetic stirrer was charged with 1,4-naphthoquinone (1) (20mmol; 3.16g), aromatic compounds (10mmol), 15mL of CH3COOH and H3PW12O40 (288mg; 1mol%). The flask was heated at 100C for 24h. After that time, the flask was cooled down to room temperature and 15mL of chloroform was added. The solution was washed with 20mL of brine. The organic phase was separated and dried by MgSO4. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel, using a gradient hexane/acetone mixture as eluent.

According to the analysis of related databases, 15799-79-8, the application of this compound in the production field has become more and more popular.

Synthetic Route of 15799-79-8, The chemical industry reduces the impact on the environment during synthesis 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, I believe this compound will play a more active role in future production and life.

[0109] (R)-3-(4-Nitro-phenyl)-3-(4-dimethylamino-2-methoxy-phenyl)-propionaldehyde (Table 1, entry 9): To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (24.6 mg, 0.100 mmol, 0.100 equiv), N,N-dimethyl-m-anisidine hydrochloride (18.8 mg, 0.100 mmol, 0.100 equiv), CH2Cl2 (1.00 ml), and N,N-dimethyl-m-anisidine (425 uL, 2.90 mmol, 2.90 equiv). The solution was cooled to -10o C. before p-nitro-cinnamaldehyde (177 mg, 1.00 mmol, 1.00 equiv) was added as a solid. After 48 h, the reaction mixture was subjected directly to silica gel chromatography. Gradient elution with 10-50% EtOAc in hexanes followed by concentration in vacuo afforded the product as a bright orange oil in 87% yield (285 mg, 0.867 mmol); 92% ee. IR (film) 2938, 2894, 2837, 2726, 1722, 1614, 1516, 1345, 1241, 1120, 1033, 980.1, 858.6, 814.9 cm-1; 1HNMR (300 MHz, CDCl3) ?9.74 (t, J=1.9 Hz, 1H, CHO), 8.12 (td, J=2.2, 9.3 Hz, 2H, ArH), 7.42 (td, J=1.5, 9.3 Hz, 2H, ArH), 6.97 (d, J=8.3 Hz, 1H, ArH), 6.30 (dd, J=2.5, 8.8 Hz, 1H, ArH), 6.24 (d, J=2.2 Hz, 1H, ArH), 4.98 (t, J=7.8 Hz, 1H, ArCH), 3.79 (s, 3H, OCH3), 3.21-3.09 (m, 2H, CH2CO), 2.96 (s, 6H, N(CH3)2); 13C NMR (75 MHz, CDCl3) ?201.2, 157.8, 152.3, 151.4, 146.5, 128.9, 128.6, 123.8, 118.0, 104.8, 96.4, 55.4, 48.4, 40.8, 38.2. HRMS (CI) exact mass calcd for (C18H20N2O4) requires m/z 328.1423, found m/z 328.1422. [?]D=0.58.1 (c=1.0, CHCl3). [0110] The enantiomeric ratio of the product was determnined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction of the aldehyde) using a Chiracel AD and AD guard column (10% ethanol/hexanes, 1 mL/min); R isomer tr=25.6 min, S isomer tr=29.5 min.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Methoxy-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.