2-Chloro-6-methylpyridine-4-carboxylic acid → (2-Chloro-6-methylpyridin-4-yl)methanol

2-Chloro-6-methylpyridine-4-carboxylic acid (0.52 g, 3.04 mmol) and borane-tetrahydrofuran complex (6.08 mL, 6.08 mmol) were combined in tetrahydrofuran (10.0 mL) at 0° C. After 15 min, the ice bath was removed and mixture stirred at room temperature for 4 h. The mixture was cooled to 0° C., and treated with methanol until no bubbles were observed. The solvents were removed and the crude mixture dissolved in ethyl acetate which was washed with water (2×), brine (2×), dried over sodium sulfate, and concentrated to afford 0.25 g (53%) which was used without purification. 1H-NMR (CDCl3, 500 MHz) δ 2.53 (s, 3H), 4.7 (s, 2H), 7.06 (s, 1H), 7.15 (s, 1H). Mass spec.: 158.0 (MH)+.

1. customthe ice bath was removed
2. temperatureThe mixture was cooled to 0° C.
3. additiontreated with methanol until no bubbles
4. customThe solvents were removed
5. dissolutionthe crude mixture dissolved in ethyl acetate which
6. washwas washed with water (2×), brine (2×)
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated
9. customto afford 0.25 g (53%) which
10. customwas used without purification

ORD record

ord-9227047f8021415cbf679569005ed71f

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569578B2