Water → (6-Methoxypyridin-3-yl)methanol

Participants

Reaction Steps

To a solution of methyl 6-methoxynicotinate (1.00 g, 5.98 mmol) in 20 mL of tetrahydrofuran at 0° C. under an atmosphere of nitrogen was added lithium aluminum hydride (1.0 M in tetrahydrofuran, 9.0 mL, 9.0 mmol) dropwise. After 30 min, the mixture was warmed to ambient temperature, and after 30 min, the mixture was cooled to 0° C., diluted with diethyl ether, and treated with water (0.34 mL), 15% aqueous sodium hydroxide (0.34 mL), and additional water (1.02 mL). The mixture was dried with magnesium sulfate and warmed to ambient temperature. After 15 min, the mixture was filtered through Celite and concentrated in vacuo to provide (6-methoxypyridin-3-yl)methanol that gave a proton NMR spectra consistent with theory.

Provenance & Evidence