Methyl 5-fluoro-2-methoxynicotinate → (5-Fluoro-2-methoxypyridin-3-yl)methanol

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Reaction Steps

To 5-fluoro-2-methoxy-nicotinic acid methyl ester (35, 10 g, 54.0 mmol) in 200 mL of tetrahydrofuran, lithium aluminum hydride (81 mL, 1 M in tetrahydrofuran, 81 mmol) was added dropwise at −78° C. and stirred for several hours. The reaction was quenched with dropwise addition of 3 mL water, 3 mL of 15% aqueous sodium hydroxide, and 10 mL of water sequentially, then 200 mL of methyl t-butyl ether was added. Solids were filtered out and the filtrate concentrated under vacuum to provide the desired compound as a white solid (36, 8 g, 50.9 mmol, 94%).

Provenance & Evidence