Water → (2-Methylpyridin-3-yl)methanol

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (2.0 g, 53 mmol) in anhydrous ether (300 ml) was added a solution of methyl-2-methylpyridine carboxylate (8.14 g, 53.8 mmol) in 100 ml anhydrous ether over 20 min. The reaction mixture was stirred 1.5 h at room temp. and the treated carefully in succession with 2 ml of water, 2 ml of 15% aqueous sodium hydroxide, and 6 ml of water. The white slurry was stirred 1 h at room temp. and then filtered through Celite. After several washings with ether, the combined filtrates were washed with brine, dried (MgSO4), and concentrated in vacuo to a pale yellow oil. This material was purified by column chromatography on silica with 5% methanol/chloroform as eluent to afford the product as a colorless oil.

Provenance & Evidence