Water → (3-(4-Chlorophenyl)-5-methylisoxazol-4-yl)methanol

Participants

Reaction Steps

To a solution of 3-(4-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (373 mg, 1.4 mmol) in THF (17.9 mL) was added portionwise lithiumaluminiumhydride (29.6 mg, 0.78 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 3 h. The mixture was then cooled to 0° C. and water (29.0 μL) added followed by sodium hydroxide (15% solution, 29.0 μL) and then again water (84.0 μL) and the mixture then stirred overnight at room temperature. The precipitate was then filtered off and washed with THF. The combined washings and filtrate were then evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (204 mg, 65%) which was obtained as a white solid. MS: m/e=224.1 [M+H]+.

Provenance & Evidence