Bromide ion → 1-(Pyridin-2-yl)hept-6-en-3-one

Participants

Reaction Conditions

Reaction Steps

While under a nitrogen atmosphere, a solution of N-methoxy-N-methyl-3-(pyridin-2-yl)propanamide (1.00 g, 5.15 mmol), in tetrahydrofuran (10 mL) was cooled to 0° C. and treated with 4-butenylmagnesiun bromide (0.5 M in THF, 16 mL, 8.0 mmol) in a dropwise manner. The solution was stirred for 1 hour at 0° C. then allowed to warm to room temperature for 3 h. The resulting solution was poured into saturated aqueous sodium chloride (100 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. Purification by flash column chromatography (silica gel, 0-25% ethyl acetate in heptane) gave 1-(pyridin-2-yl)hept-6-en-3-one as a colorless oil (828 mg, 85%). ESI MS found for C12H15NO m/z [190.1 (M+1)].

Provenance & Evidence