Methyl 2-methylnicotinate → (2-Methylpyridin-3-yl)methanol

Participants

Reaction Steps

To a slurry of lithium aluminum hydride (500 mg, 13.2 mmol) in anhydrous tetrahydrofuran (45 mL) at 0° C. under nitrogen was added dropwise a solution of methyl 2-methylnicotinate (17, 1.0 g, 6.6 mmol) in anhydrous tetrahydrofuran (5 mL). After 1 h the suspension was diluted with water (1 mL) and 6 N NaOH solution (5 mL). The precipitate was removed by vacuum filtration and the filtrate was dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to provide the title compound as a light yellow oil: 1H NMR (300 MHz) 8.37 (d, J=4.9 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H), 7.14 (dd, J=7.6 Hz, 4.9 Hz, 1H), 4.72 (s, 2H), 2.95-2.74 (bs, 1H), 2.53 (s, 3H) ppm.

Provenance & Evidence