2-Acetylpyridine → alpha-Methyl-2-pyridinemethanol

Temperature

25 °C

To an ice-cooled solution of 1-(pyridin-2-yl)ethanone (11 g, 91 mmol) in methanol (120 mL) was slowly added sodium borohydride (8.58 g, 227 mmol). Upon complete addition, the mixture was warmed to 25° C. After 16 h, the reaction was diluted with water (100 mL), and the mixture was concentrated in vacuo. The resulting aqueous solution was extracted with ethyl acetate (3×100 mL). The combined organic extracted were washed with saturated aqueous sodium chloride (2×50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (10→30% ethyl acetate in petroleum ether) afforded 1-(pyridin-2-yl)ethanol (10.3 g, 92% yield). 1H NMR (400 MHz, Chloroform-d) δ 8.54 (d, J=4.8 Hz, 1 H), 7.72-7.68 (m, 1 H), 7.30 (d, J=8.0 Hz, 1 H), 7.22-7.20 (m, 1 H), 4.93-4.88 (m, 1 H), 4.39 (br s, 1 H), 1.52 (d, J=6.4 Hz, 3 H).

1. additionUpon complete addition
2. concentrationthe mixture was concentrated in vacuo
3. extractionThe resulting aqueous solution was extracted with ethyl acetate (3×100 mL)
4. extractionThe combined organic extracted
5. washwere washed with saturated aqueous sodium chloride (2×50 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by flash column chromatography (10→30% ethyl acetate in petroleum ether)

ORD record

ord-81ea466aaefa488096734cd601ffd991

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365583B2