GENERAL STEPS: To a round-bottomed flask containing 3-fluoropyridine-2-aldehyde (400 mg, 3.20 mmol) was added a methanolic solution of sodium methanolate (15 mL, 7.50 mmol, 0.5 M). The reaction mixture was stirred at 80 °C for 4 hours. Upon completion of the reaction, the mixture was cooled to 0 °C in an ice bath, followed by the addition of sodium borohydride (90 mg, 2.38 mmol) and continued stirring at 0 °C for 20 min. After termination of the reaction, ice water was added to the mixture. The solvent was removed by concentration under reduced pressure and the resulting residue was purified by ISCO medium pressure liquid chromatography (MPLC) with an elution gradient of 40-100% ethyl acetate/hexane to afford (3-methoxypyridin-2-yl)methanol as a white solid (200 mg, 45.0% yield). The product was characterized by 1H NMR (DMSO-d6): δ 8.11 (dd, 1H), 7.41 (dd, 1H), 7.31 (dd, 1H), 4.83 (t, 1H), 4.54 (d, 2H), 3.82 (s, 3H). Mass spectrometry (MS) showed the molecular ion peak (M+H)+ m/z = 140.
