Ethyl Thioglycolate → Tert-butyl 2-(ethoxycarbonylmethylthiomethyl)acrylate

Participants

Reaction Steps

To a stirred solution of ethyl α-mercaptoacetate (1.6 g) in ethanol (15 ml), potassium tert-butoxide (1.5 g) was added at -10°-0° C. under nitrogen atmosphere, and the mixture was stirred for 10 minutes at room temperature. Under ice-cooling, tert-butyl 2-bromomethylacrylate (2.9 g) dissolved in ethanol (5 ml) was added to the reaction mixture and the mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 2.1 g (60%) of tert-butyl 2-(ethoxycarbonylmethylthiomethyl)acrylate.

Provenance & Evidence