Electric Literature of 171290-52-1, 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. 171290-52-1 name is 3,5-Dimethoxyphenylacetylene, 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.
Example 3: Synthesis of 3,4′,5-trimethoxydiphenylacetylene5 ml of pyrrolidine (99 %) were placed in a 10 ml glass tube fitted with a septum, a magnetic stirring bar and an argon supply. The pyrrolidine was degassed with argon for 30 minutes at room temperature. Afterwards 240 mg of 4-iodoanisol (98 %, 1 .01 mmol, 1 .00 eq.), 12 mg of triphenylphosphine (97 %, 0.044 mmol, 0.044 eq.), 40 mg of palladium on charcoal (10 %, 0.038 mmol, 0.037 eq.) and finally 249.3 mg of 1 -ethynyl-3,5-dimethoxybenzene (98 %, 1 .51 mmol, 1 .50 eq.) were added to the presented pyrrolidine.The mixture was stirred under argon at 85 0C (aluminum block temperature) for 17 hours. The reaction solution was cooled to room temperature and then 10 ml of ethyl acetate were added. Afterwards the suspension was filtrated with a membrane filter (0.45 mum).The solution was treated with 20 ml of a saturated ammonium chloride solution. Then an extraction was performed by extracting twice with 20 ml of ethyl acetate. The organic solutions were dried with sodium sulfate and afterwards concentrated at 40 0C and 180 mbar. The dark yellow crude material was purified by chromatography with ethyl acetate and n-heptane in a ratio of 5:95. The product containing fractions were collected and concentrated at 40 C and 90 mbar. The purified product was analyzed by GC-MS and NMR. The yield was 75 % based on the 4-iodoanisole. GC/MS: Retention time: 21 .61 min, Area %: 99.10 %; M: M+ 268, 253, 225, 210, 195, 182, 167, 152, 139.1H-NMR 300 MHz, d-Chloroform) delta 3.82 ppm (s, 6H, OCH3), 3.85 ppm (s, 3H, OCH3), 6.47 (t, J=2.31 Hz, 1 H, ArH), 6.70 ppm (d, J=2.31 Hz, 2H, ArH), 6.88 – 6.89 ppm (m, 2H, ArH), 7.48 – 7.52 ppm (m, 2H, ArH). 13C-NMR 75 MHz, d- Chloroform) delta 55.30 (OCH3), 56.42 (2xOCH3), 88.10 (C), 89.00 (C), 101 .57 (C), 109.22 (2xCH3), 1 14.02 (2xCH3), 1 15.20 (C), 124.91 (CH), 133.12 (2xCH), 159.71 (C), 160.55 (2xC).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dimethoxyphenylacetylene, and friends who are interested can also refer to it.
Reference:
Patent; DSM IP ASSETS B.V.; LETINOIS, Ulla; BONRATH, Werner; WO2011/9888; (2011); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem