These common heterocyclic compound, 24332-20-5, name is 1,1,2-Trimethoxyethane, 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. category: ethers-buliding-blocks
Step A: Preparation of (Z)-3-(dimethylamino)-2-methoxyacrylaldehyde: The reaction was carried out in a 3-neck flask (500 mL) equipped with an internal thermometer. PCl5 (64.4 g, 294 mmol) was added in small portions (~5 g) to a cold (0 C.) solution of 1,1,2-trimethoxyethane (36 g, 294 mmol) while keeping the internal temperature below 30 C. The mixture was heated to 60 C. for 75 minutes and then placed in an ice bath. DMF (66 mL, 852 mmol) was added via a dropping funnel while maintaining the internal temperature below a temperature of 10 C. The mixture was stirred at room temperature for 40 hours, and MeOH (100 mL) was added dropwise via a dropping funnel while keeping the internal temperature below 10 C. The solution was transferred to an addition funnel and was added dropwise to a 30% solution of sodium methoxide (403 mL, 2.17 mol) in MeOH while maintaining the internal temperature below 20 C. The mixture was heated at reflux for 4 hours and then concentrated. The residue was taken up in water (500 mL) and extracted with dichloromethane (500 mL*3). The combined organics were dried, filtered and concentrated to give the desired product (19 g, 25%). MS (APCI-pos) M+1=130.0.
The synthetic route of 1,1,2-Trimethoxyethane has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Array Biopharma, Inc.; US2010/63066; (2010); A1;,
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