General procedure for the synthesis of 2-chloro-6-hydroxymethylpyridine from methyl 6-chloropyridine-2-carboxylate: 6.7 g (39.0 mmol) of methyl 6-chloropyridine-2-carboxylate was dissolved in 90 mL of anhydrous tetrahydrofuran, which was subsequently cooled to -45 °C. A 40 mL solution of 1 M lithium aluminum hydride in tetrahydrofuran was added slowly and dropwise over 30 min. The reaction mixture was stirred at -45°C for 30 minutes and then slowly warmed to 0°C and continued stirring for 30 minutes. Subsequently, 15 mL of 1 N aqueous sodium hydroxide solution was slowly added dropwise to quench the reaction. Solid impurities were removed by diatomaceous earth filtration and the filtrate was concentrated to give 5.08 g (35.4 mmol, 91% yield) of 2-chloro-6-hydroxymethylpyridine. The product was characterized by 1H NMR (CDCl3, ppm): δ 7.61 (1H, d), 7.30 (1H, t), 7.04 (1H, d), 3.72 (2H, s).FAB MS (m/z) = 144 [M + 1].
