Imidazole → ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]acrylate

Participants

Reaction Steps

To a suspension of ethyl 2-[(1R)-1-hydroxyethyl]acetylate (11.22 g) and imidazole (6.89 g) in N,N-dimethylformamide (110 ml) was added portionwise t-butyldimethylsilyl chloride (14.08 g) at 0° C. After the mixture was stirred for 10 hours, the reaction mixture was poured into a mixture of water and ethyl acetate. The water layer was separated and extracted twice with ethyl acetate. The combined organic layers were washed with water, 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate, water and an aqueous sodium chloride, and then, dried over magnesium sulfate. The resultant solution was evaporated, and the residue was distilled to give ethyl 2-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-acrylate (19.53 g).

Provenance & Evidence