Ethyl 4-chloro-2-ethylpyridine-3-carboxylate → (4-Chloro-2-ethylpyridin-3-yl)methanol

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Reaction Steps

Lithium aluminum hydride (234 mg, 6.2 mmol) was stirred in anhydrous THF (30 mL). A solution of ethyl 4-chloro-2-ethylpyridine-3-carboxylate (878 mg, 4.1 mmol) in anhydrous THF (5 mL) was added at 0° C., and the reaction mixture was stirred at room temperature for 1.5 hours. The reaction was quenched with an aqueous solution of sodium hydroxide and extracted 5 times with ethyl acetate. The combined organic phase was washed with brine and dried over sodium sulfate. After evaporation of the solvent, (4-chloro-2-ethylpyridin-3-yl)methanol was obtained as an oil (601 mg, 85% yield) and used in the next step without further purification.

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