Iodoethane → Ethyl 2-ethoxypyridine-3-carboxylate

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Reaction Steps

A suspension of the compound prepared in Example 284 (1.3 g) and cesium carbonate (2.53 g) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 2 hours and then treated with ethyl iodide (0.62 mL) at room temperature, and stirring continued for 18 hours. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and saturated aqueous solution of sodium bicarbonate. The combined organic extracts were washed with brine, dried and evaporated in vacuo to a yellow oil and purified by column chromatography on silica gel (10-50% ethyl acetate in hexane) to obtain the title compound (0.904 g) having the following physical data.

Provenance & Evidence