The general procedure for the synthesis of 3-hydroxymethyl-4-methylpyridine from 4-methylpyridine-3-carboxylic acid was as follows: a tetrahydrofuran solution (15 mL) of 1.0 mol/L borane-tetrahydrofuran complex was slowly added to a tetrahydrofuran solution (15 mL) containing 4-methylnicotinic acid (686 mg), followed by a heating and refluxing for 2 hours. Upon completion of the reaction, 2.0 mol/L hydrochloric acid solution (5 mL) was added dropwise to the reaction system and refluxing was continued for 0.5 hours. After the reaction mixture was cooled to room temperature, it was extracted with ethyl acetate. The organic phase was washed sequentially with aqueous sodium carbonate solution and saturated aqueous sodium chloride solution, followed by drying with anhydrous sodium sulfate. After the solvent was removed by distillation under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent ratio: ethyl acetate:methanol=1:0→9:1), and the target product (4-methylpyridin-3-yl)methanol (270 mg) was finally obtained as a white solid. Mass spectrum (ESI m/z): 124 (M+H). Retention time (min): 1.11.
