Aluminium lithium hydride → HCID 67121090, compound

To a solution of ethyl 5-(3-fluoro-4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate (2.0 g, 6.60 mmol) in tetrahydrofuran (25 mL) was added lithium aluminium hydride (375 mg, 9.89 mmol) and the reaction mixture was stirred for 2 hours at room temperature. The reaction was quenched by the addition of water (0.18 mL) followed by an aqueous solution of 1N NaOH (0.18 mL) and finally water (0.54 mL) over a 30 minute period. The resultant viscous grey slurry was diluted with diethyl ether (50 mL) and stirred for 30 minutes before filtering through a celite pad. The cake was washed with diethyl ether (3×70 mL) and the filtrate evaporated to dryness in vacuo to obtain (5-(3-fluoro-4-(trifluoromethyl)phenyl)isoxazol-3-yl)methanol (1.43 g, 5.48 mmol).

1. customThe reaction was quenched by the addition of water (0.18 mL)
2. waitfollowed by an aqueous solution of 1N NaOH (0.18 mL) and finally water (0.54 mL) over a 30 minute period
3. additionThe resultant viscous grey slurry was diluted with diethyl ether (50 mL)
4. stirringstirred for 30 minutes
5. filtrationbefore filtering through a celite pad
6. washThe cake was washed with diethyl ether (3×70 mL)
7. customthe filtrate evaporated to dryness in vacuo

ORD record

ord-7bf0e592ac084685a280556f9f6ac164

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211927B2