Methanol → 5-Fluoro-2,3-dihydro-1H-inden-1-ol

Temperature

0 °C

Charged 5-fluoro-2,3-dihydroinden-1-one (486 mg, 3.22 mmol), methanol (8 mL) and dichloromethane (4 mL) to a flask, the mixture was cooled to 0° C. and NaBH4 (119 mg, 3.22 mmol) was added in portions. The reaction mixture was stirred at 0° C. for 15 min, warmed up to room temperature and stirred for 30 min. Added water, extracted with ethyl acetate twice, and washed the organic phase with brine and dried with anhydrous Na2SO4, concentrated to give the title compound (488 mg, 100%). 1H NMR (400 MHz, CDCl3): δ 1.94-2.02 (1H, m), 2.46-2.55 (1H, m), 2.76-7.84 (1H, m), 3.01-3.08 (1H, m), 5.20 (2H, t, J=5.6 Hz), 6.89-6.93 (2H, m), 7.32-7.36 (1H, m).

1. temperaturewarmed up to room temperature
2. stirringstirred for 30 min
3. extractionAdded water, extracted with ethyl acetate twice
4. washwashed the organic phase with brine
5. dry with materialdried with anhydrous Na2SO4
6. concentrationconcentrated

ORD record

ord-650772afde2144ac8e6af8ef7145e2c8

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09107916B2