General procedure for the synthesis of 2-fluoro-4-pyridinemethanol (37) from 2-fluoro-4-pyridinecarboxylic acid phenylmethyl ester (36) (4.536 g, 19.62 mmol): to a stirred solution of 2-fluoro-4-pyridinecarboxylic acid phenylmethyl ester (36) in anhydrous methanol (40 mL) was added sodium methanolate (1.06 g, 19.62 mmol) under ice bath cooling. After stirring for 30 min, an excess of ammonium chloride was added to the reaction mixture. Subsequently, the mixture was concentrated by evaporation under vacuum and the residue was purified by silica gel column chromatography (eluent: ether/hexane, 1:1, v/v) to afford 2.34 g (94% yield) of 2-fluoro-4-pyridinylmethanol (37) as a white solid with a melting point of 70-71°C. 1H NMR (200 MHz, CDCl3) δ: 2.40 (1H, t, J = 4.0 Hz), 4.78 (2H, d, J = 4.0 Hz), 6.97 (1H, s), 7.15 (1H, m), 8.15 (1H, d, J = 5.0 Hz); Mass Spectrum (EI): m/z 127 (M+).
