Water → 1-(5-Fluoropyridin-2-yl)ethan-1-ol

1-(5-Fluoropyridin-2-yl)ethanone (Method 1; 11.3 g, (75% pure), 60.9 mmol) in MeOH was added sodium boronhydride (2.30 g, 60.9 mmol) potion wise at 0° C. After adding, the reaction was warmed to room temperature and stirred at room temperature for 1 hour. Water (10 ml) was added and the solution was extracted with ether (2×50 ml). The combined organic layers were dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (ether) to give the title compound as a clear oil (7.5 g, 87%). 1H NMR (400 MHz) 8.46 (d, J=3.2 Hz, 1H), 7.69 (ddd, J=3.2, 3.2 and 3.2 Hz, 1H), 7.55 (m, 1H), 5.44 (d, J=4.4 Hz, 111), 4.73 (m, 1H), 1.34 (d, J=6.4 Hz, 3H).

1. additionAfter adding
2. extractionthe solution was extracted with ether (2×50 ml)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. customAfter removal of solvent
5. customthe resulted residue was purified by column chromatography (ether)

ORD record

ord-f81a88fb3f8549e5a40c9971cc6b617a

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114989B2