Water → (5-Methylpyridin-3-yl)methanol

Participants

Reaction Steps

Lithium aluminum hydride (552 mg, 14.5 mmol) was suspended in tetrahydrofuran (10 mL). To this, a tetrahydrofuran solution (10 mL) of methyl 5-methyl nicotinate (1.00 g, 14.5 mmol) was slowly added at 0° C. and the mixture was stirred at the same temperature for 30 minutes. The reaction was stopped by successive addition of water (0.552 mL), a 15% aqueous sodium hydroxide solution (0.552 mL) and water (1.66 mL) to the reaction mixture. The mixture was stirred at room temperature for 30 minutes and then filtered through Celite. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give 3-hydroxymethyl-5-methylpyridine (972 mg, yield: 100%).

Provenance & Evidence