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

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Reaction Steps

To a slurry of lithium aluminum hydride (0.45 g, 11.9 mmol) in anhydrous diethyl ether (40 mL) at 0° C., a solution of 2-chloro-6-methylpyridine-4-carboxylic acid (2.0 g, 11.7 mmol) in diethyl ether (30 mL) was added. The resulting mixture was stirred at room temp. overnight, and quenched with successive addition of water (0.45 mL), 15% aqueous NaOH (0.45 mL), and water (1.35 mL). The resultant slurry was stirred at room temp. for 30 min., and filtered through a small plug of Celite. The filtrate was washed brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide 2-chloro-4-hydroxymethyl-6-methylpyridine.

Provenance & Evidence