Sodium borohydride → (5-(4-(Trifluoromethyl)phenyl)-4,5-dihydroisoxazol-3-yl)methanol

To a stirred mixture of sodium borohydride (378 mg, 10.0 mmol) in ethanol (20 ml) was added slowly a solution of ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate (1.6 g, 5.75 mmol) in ethanol (10 mL). The resulting reaction mixture was stirred under an atmosphere of nitrogen for 8 hours. Ethanol was removed under reduced pressure and water (20 ml) added. The aqueous mixture was acidified to about pH 3 with concentrated HCl, and the acidic solution extracted with ethyl acetate (3×20 ml). The resulting organic phase was washed with saturated aqueous sodium bicarbonate (20 ml), 30% aqueous ammonium chloride(20 ml), brine, dried over sodium-sulfate, concentrated, and purified using chromatography (3% MeOH in CH2Cl2) to afford (5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazol-3-yl)methanol (1.1 g, M+1=246.1).

1. customThe resulting reaction mixture
2. customEthanol was removed under reduced pressure and water (20 ml)
3. additionadded
4. extractionthe acidic solution extracted with ethyl acetate (3×20 ml)
5. washThe resulting organic phase was washed with saturated aqueous sodium bicarbonate (20 ml), 30% aqueous ammonium chloride(20 ml), brine
6. dry with materialdried over sodium-sulfate
7. concentrationconcentrated
8. custompurified

ORD 기록

ord-462b83e0aa924d4bb79f599a9119fbea

출처 데이터셋

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07026321B2