Sodium hydride → 2-(6-Ethoxypyridin-3-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (6-chloro-3-pyridinyl)acetic acid (0.094 g, 0.545 mmol) in EtOH (1.6 mL) was added 3.1 M EtONa in EtOH (0.7 mL, 2.17 mmol) and the reaction mixture was stirred at 100° C. room temperature for 24 hours after which an excess of NaH (60% dispersion in oil) was added together with 1 mL EtOH and heating at 100° C. was continued for 96 h. The solvent was evaporated in vacuo and the residue was taken up into diethyl ether (5 mL). The organic phase was washed with diluted HCl (2×2 mL) and brine (2 mL), dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (0.081 g, 82%) as a pale brown solid, which was used without further purification. 1H NMR (CDCl3): δ 10.06 (br s, 1H), 8.06 (s, 1H), 7.55 (d, J=9.2 Hz, 1H), 6.72 (d, J=8.4 Hz, 1H), 4.30 (q, J=6.1 Hz, 2H), 3.58 (s, 2H) 1.38 (t, J=8.0, 3H). MS (ESI) (M+H)+=182.

Provenance & Evidence