Hydrochloric Acid → 3-Isoxazolemethanol,5-(trifluoromethyl)-(9CI)

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Reaction Steps

To a solution of 7.5 g 5-trifluoromethyl-isoxazole-3-carboxylic acid ethyl ester in 85 mL ethanol was added 3.66 g sodium hydride portion wise at RT. The reaction mixture was stirred at RT for 16 h. 100 mL 1M HCl were added drop by drop under ice-bath cooling. The reaction mixture was extracted with 250 mL diethyl ether and 200 mL sat. NaCl solution/water mixture 1:1. The aqueous layer was back-extracted with diethyl ether (2×100 mL). The org. layers were washed with sat. NaCl solution/water mixture 1:1 (2×200 mL). The combined org. layer was dried over Na2SO4, filtered off and concentrated in vacuo to yield 5.8 g of the title compound as brown oil. MS (EI): 167 (M+H)+.

Provenance & Evidence