Chloromethyl ethyl ether → 2-Chloro-6-(ethoxymethoxy)pyridine

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To a solution of 13.4 g (0.1 mol) of 6-chloro-2-pyridinol in 200 mL methylene chloride at -23° C. was added 3 g sodium hydride (80%, 0.1 mol) slowly, and stirring was continued for 5 min. 10 mL of Chloromethyl ethyl ether (0.11 mol) was added dropwise at -23° C. After stirring for 15 min. at -23° C., and an additional 1 hr at room temperature, the reaction was quenched with 50 mL of water. The mixture was extracted with two 50 mL portions of methylene chloride, and the combined organic layers were washed with water and brine. After drying over sodium carbonate, the solvents were evaporated under reduced pressure. The residue was purified by radial PLC (5% ethyl acetate/hexanes) to give 7.78 g (42%) of product as a colorless oil (bp 72° C., 0.25 mmHg) and 2.14 g of recovered starting material. 1H NMR (300 MHz, CDCl3) δ7.55 (t, 1H, J=7.7 Hz), 6.94 (d, 1H, J=8.5 Hz), 6.71 (d, 1H, J=8.0 Hz), 5.55 (s, 2H), 3.77 (q, 2H, J=7.1 Hz), 1.25 (t, 3H, J=7.1 Hz). 13C NMR (75 MHz, CDCl3) δ162.4, 148.5, 141.0, 117.2, 109.3, 91.4, 65.7, 15.2. Analysis Calculated for C8H10ClNO2 : C, 51.21; H, 5.37; N, 7.47. Found: C, 51.33; H, 5.35; N, 7.46.

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