[Synthesis]
GENERAL STEPS: To a stirred N,N-dimethylformamide (30 mL) solution of 6-chloropyridin-3-ol (3.0 g, 23.2 mmol) at 0 °C, ethyl iodide (4.33 g, 27.8 mmol, 2.22 mL) and potassium carbonate (9.60 g, 69.6 mmol) were sequentially added. The reaction mixture was gradually warmed to 40 °C and stirred continuously at this temperature for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (30 mL) and subsequently extracted with ethyl acetate (60 mL x 3). The organic phases were combined, washed with saturated aqueous sodium chloride (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-chloro-5-ethoxypyridine (3.30 g, 20.9 mmol, 90% yield) as a yellow solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.97 (d, J=2.9Hz, 1H), 7.17-7.07 (m, 2H), 3.99 (q, J=7.0Hz, 2H), 1.36 (t, J=7.0Hz, 3H). |