Sodium methanolate (0.065 g, 1.2 mmol) and 1-(2-chloropyridin-3-yl)ethanone (0.063 g, 0.4 mmol) were dissolved in anhydrous methanol (1.5 mL) in a 7 mL vial under the protection of nitrogen and the reaction was stirred for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was terminated by the addition of 0.5 mL of water. Subsequently, methanol was removed by concentration using a rotary evaporator and the remaining aqueous phase mixture was extracted by partitioning with dichloromethane (20 mL) and water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated again using a rotary evaporator to afford the crude product 1-(2-methoxypyridin-3-yl)ethanone as an orange oil (0.032 g, 53% yield), which could be used in subsequent reactions without further purification. The structure of the product was confirmed by 1H-NMR (CDCl3) and mass spectrometry (ESI+): 1H-NMR (CDCl3) δ 8.33 (dd, J = 4.8 and 2.0 Hz, 1H), 8.13 (dd, J = 7.5 and 2.0 Hz, 1H), 7.00 (dd, J = 7.5 and 4.8 Hz, 1H), 4.08 (s, 3H), and 2.67 (s, 3H); MS (ESI+): m/z (M + H)+ = 152.
