Water → HCID 23725856, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methyl-3-phenyl-4-[1-(4-trifluoromethyl-phenyl)-1H-imidazol-4-yl]-isoxazole (950 mg, 2.6 mmol) in THF (50 mL) at −78° C. was added BuLi (1.6 M in hexane, 2.4 mL, 3.9 mmol) and the resulting mixture allowed to warm up to −25° C. over 20 min and then re-cooled to −78° C. Then ethyl chloroformate (474 mg, 4.4 mmol) was added and the resulting mixture allowed to warm up to −25° C. over 3 h and then warmed up to 0° C. whereupon water was added. The reaction mixture was then extracted with ethyl acetate and the combined organic layers were then washed with a saturated solution of sodium hydrogen carbonate, brine and then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 80:20) afforded the title compound (232 mg, 18%) which was obtained as an off-white foam. MS: m/e=442.5 [M+H]+.

Provenance & Evidence