Ammonium Chloride → 4-Ethynyl-5-methyl-3-phenyl-isoxazole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(2,2-dibromo-vinyl)-5-methyl-3-phenyl-isoxazole (1.0 g, 2.92 mmol) in THF (6 mL) was added dropwise isopropylmagnesium chloride solution (2M in THF, 2.92 mL, 5.84 mmol) and the resulting solution stirred under argon for 1 h at 0° C. Saturated aqueous ammonium chloride (15 mL) was added and the resulting mixture extracted with ethyl acetate (3×25 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane) afforded the title compound (486 mg, 91%) which was obtained as a yellow oil. MS: m/e=184.2 [M+H]+.

Provenance & Evidence