Sodium ethoxide → HCID 14267835, compound

Participants

Reaction Steps

A solution of ethyl N-(b-ethoxycarbonylethyl)-N-(4-methoxyphenyl)glycinate (106.7 g, 0.345 mol) in dry benzene (400 mL) is added to a mixture of ethanolic sodium ethoxide in benzene (prepared by dissolving 13.1 g of sodium metal in 300 mL of ethanol and then the ethanolic sodium ethoxide solution is diluted with 500 mL of benzene) at room temperature over a period of 90 minutes. The mixture is heated at reflux for 30 minutes and then is cooled to room temperature. The solid is collected by filtration, and then is suspended in an ice-water mixture (1 L). The mixture, after being neutralized with 1 N hydrochloric acid, is extracted with diethyl ether (3×500 mL). The combined extracts are washed with water, dried over sodium sulfate, concentrated, and the residue is crystallized from n-hexane-diethyl ether to afford 1-(4-methoxyphenyl)-4-ethoxycarbonylpyrrolidine-3-one (87.4 g, 64%), mp 58°-60° C. 1H NMR (CDCl3) d 1.34 (3H, dt, CH2Me), 3.76 (3H, s, OMe), 3.75 (2H, dq, CH2Me), 4.14 (2H, s, 2-CH2), 4.12-4.39 (3H, m, H-4 and 5-CH2), 6.46 and 6.86 (each 2H, m, Ph).

Provenance & Evidence