To a tetrahydrofuran (THF, 30 mL) solution of methyl 6-chloronicotinate (1.08 g, 0.009 mol) was added dropwise lithium aluminum hydride (1 M solution of THF, 7.5 mL, 0.0075 mol) at 0 °C and under nitrogen protection. The reaction mixture was gradually warmed to room temperature and stirred continuously for 3 hours. Subsequently, the reaction mixture was cooled to 0 °C, diluted with ethyl acetate and the reaction was quenched by slow addition of water (2 mL). The mixture was filtered through a bed of diatomaceous earth and the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by fast column chromatography with the eluent ethyl acetate:hexane (40:60, v/v) to give the target compound 2-chloro-5-hydroxymethylpyridine. Yield: 0.55 g. 1H-NMR (CDCl3, 400 MHz) δ ppm: 2.09 (broad peak, 1H), 4.72 (single peak, 2H), 7.31-7.34 (double peak, J = 8.1 Hz, 1H), 7.68-7.71 (double-double peak, J = 2.2, 8.4 Hz, 1H), 8.36 (single peak, 1H). Mass spectra (m/z): 144.1, 146.0 ([M + H]+).
