Hydrochloric Acid → HCID 59331469, compound

Participants

Reaction Steps

To a solution (10 mL) of (2E)-2-[4-(cyclopropylsulfonyl)phenyl]-N-methoxy-N-methyl-3-(tetrahydro-2H-pyran-4-yl)propan-2-enamide (1.13 g) in tetrahydrofuran was added vinylmagnesium bromide (1.0M tetrahydrofuran solution, 9 mL) under ice-cooling, and the mixture was warmed to room temperature and stirred overnight. An excess amount of 1M hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (426 mg, yield 41%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). MS: 347 (MH+).

Provenance & Evidence