Acetyl chloride → 1-(3-Phenyl-5-trifluoromethyl-isoxazol-4-yl)-ethanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-phenyl-4-(1-phenyl-1H-imidazol-4-yl)-5-trifluoromethyl-isoxazole (5.0 g, 23 mmol) in 1,2-dimethoxyethane (50 mL) was added BuLi (1.6 M in hexane, 22 mL, 35 mmol) at −78° C. and the resulting mixture stirred for 1 h allowing to warm up to −35° C. and then re-cooled to −78° C. To this mixture was then rapidly added a solution of copper(I) cyanide (2.1 g, 23 mmol) containing lithium chloride (1.99 g, 47 mmol) in dry THF (30 mL) and then allowed to warm up to −35° C. and then this mixture was added to a solution of acetyl chloride (9.2 g, 8.37 mL, 117 mmol) in dry THF (50 mL) at room temperature. After 4 h at room temperature the mixture was diluted with aqueous sodium carbonate and the mixture was extracted with ethyl acetate and the combined organic layers washed with brine, dried over sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 4:1) afforded the title compound (4.86 g, 82%) which was obtained as a light yellow oil. MS: m/e 254.2 [M+H]+.

Provenance & Evidence