Sodium Bicarbonate → (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane

Participants

Reaction Steps

To a solution of 1.38 g (10.4 mmol) of aluminum chloride in 10 ml of dimethyl sulfide (Me2S) was added, with cooling with ice, a solution of 267 mg (1 mmol) of (1R,2S)-1-cyano-2-hexyl-1-(4-methoxyphenyl)cyclopropane in 10 ml of dichloromethane. This mixture was stirred with heating for 30 minutes. Saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the mixture was then subjected to extraction with 250 ml of ethyl acetate. The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and then concentrated. The residue was separated and purified by column chromatography (Kieselgel 60, hexane/ethyl acetate=5/1), thereby obtaining 197 mg (yield 81%) of (1R,2S)-1-cyano-2-hexyl-1-(4-hydroxyphenyl)cyclopropane.

Provenance & Evidence