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

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)+.

1. temperaturecooling
2. extractionThe reaction mixture was extracted with 250 mL diethyl ether and 200 mL sat. NaCl solution/water mixture 1:1
3. extractionThe aqueous layer was back-extracted with diethyl ether (2×100 mL)
4. washlayers were washed with sat. NaCl solution/water mixture 1:1 (2×200 mL)
5. dry with materiallayer was dried over Na2SO4
6. filtrationfiltered off
7. concentrationconcentrated in vacuo

ORD record

ord-30fdb0c6029840dcabe3bb5268e6af88

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729105B2