Ethanol → Ethyl 5-ethoxypyridine-2-carboxylate

Participants

Reaction Steps

To a solution of ethyl 5-bromopyridine-2-carboxylate 2 (1.5 g, 6.5 mmol) in 20 mL of EtOH was added a solution of sodium (0.18 g, 7.8 mmol) in 20 mL of EtOH. The mixture was stirred at reflux for 3 h. After removal of all solvent, the residue was purified by column (2:1 of hexane/ethyl acetate) to give ethyl 5-ethoxypyridine-2-carboxylate 3 as an oil. Yield: 0.26 g, 20%. 1HNMR (CDCl3) δ (ppm): 8.38 (d, 1H), 8.10 (d, 1H), 8.23 (d, 1H), 7.22 (dd, 1H), 4.45 (m, 2H), 4.25 (m, 1H), 1.40 (m, 6H).

Provenance & Evidence