Acrylonitrile → Ethyl 2-(2-cyanoethyl)-3-oxobutanoate

Participants

Reaction Steps

A solution of solid sodium metal (450 mg, 19.75 mmol) in EtOH at 30° C. was treated with ethyl acetoacetate (103 g, 790 mmol) maintaining temperature. Then acrylonitrile (41.9 g, 790 mmol) was added dropwise over 15 minutes. The reaction was capped and stirred for 4 hours. The solution was concentrated and the resulting solid was dissolved in 20 mL of water and 3 mL of acetic acid, and washed with 50 mL of DCM. The organic layer was dried over Na2SO4 and concentrated to an oil. Distillation was performed under reduced pressure (0.5 mm) with a bath temperature of 80° C. Fractions were collected and concentrated to provide A-1 as a colorless oil. Data for A-1: LC/MS: m/z (M+H)=183.87 found; 183.20 required

Provenance & Evidence