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

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-methyl-isonicotinic acid (13-1, 2.00 g, 11.7 mmol) was dissolved in 10 mL of anhydrous THF under N2. The solution was cooled to 0° C., and borane-THF (1 M solution in THF, 14.0 mL, 14.0 mmol) was added slowly. The reaction was heated to reflux. After 3 hours the reaction was cooled to room temperature and quenched slowly with 1M HCl (aq) until cessation of bubbling. The pH of the solution was adjusted to 7 with saturated NaHCO3 (aq). The mixture was extracted 3× with EtOAc and the extracts dried over Na2SO4, filtered and concentrated to afford (2-chloro-6-methyl-pyridin-4-yl)-methanol. 1H NMR (CDCl3) δ 7.16 (s, 1H), 7.06 (s, 1H), 4.70 (d, 2H, J=5.8 Hz), 2.53 (s, 3H), 1.95 (t, 1H, J=5.8 hz).

Provenance & Evidence