Triethylamine → 3-(4-Chloro-phenyl)-isoxazol-4-ylmethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(4-chloro-phenyl)-isoxazole-4-carboxylic acid (40.0 g, 178.9 mmol) in THF (370 mL) at −10° C. was added triethylamine (25.1 mL, 179 mmol) and then a solution of ethylchloroformate (17.4 mL, 179 mmol) in THF (111 mL) added keeping the temperature below −5° C. After 1 h the mixture was filtered and the filtrate cooled to −10° C. and a suspension of sodiumborohydride (17.6 g, 447 mmol) in water (111 mL) added over 15 minutes keeping the temperature below −5° C. The mixture was then allowed to warm up to room temperature over 2 h and diluted with aqueous sodium hydroxide (1 N, 648 mL) and extracted with tert-butylmethylether. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:1) afforded the title product (17.3 g, 46%) which was obtained as a light green solid. MS: m/e=210.1 [M+H]+.

Provenance & Evidence