Sodium ethoxide → HCID 20534011, compound

Participants

Reaction Steps

1-[(4-Chloro-7-oxo-1,3,5-cycloheptatrien-1-yl)amino]-1,3-butanedione (480 mg) was suspended in a solution of sodium ethoxide (prepared from 46 mg of sodium and 2 ml of anhydrous ethanol). The solution was heated at reflux for 3 hr. The reaction mixture was cooled and filtered. The filtrate was evaporated to dryness. The residue was dissolved in water. The solution was rendered acidic with 6 N aqueous HCl. The precipitate was collected and dried to give 3-acetyl-6-chloro-1,2-dihydro-2-oxocyclohepta[b]pyrrole, nmr (DMSO-d6) δ2.55 (s, 3H), 7.3-7.95 (m, 3H), 8.9 (d, 1H). The latter compound (5.8 g) was added to a stirred solution of sodium hydride (77 mg, 50% suspension in mineral oil) and DMF (10 ml), the solution having been stirred at 25° C. for 30 min prior to the addition. Thereafter, ethyl bromoacetate (400 mg) was added to the mixture. The mixture was heated at 100°-105° C. for 1.5 hr, cooled, diluted with water and extracted with chloroform. The residue was purified by chromatography on silica gel using methylene chloride-ethyl acetate (9:1) as the eluant. The pure fractions were pooled to give 3-acetyl-6-chloro-1,2-dihydro-2-oxocyclohepta[b]pyrrole-1-acetic acid ethyl ester, nmr (CDCl3) δ1.3 (t, 3H), 2.7 (s, 3H), 4.2 (q, 2H), 4.85 (s, 2H), 7.6 (m, 4H).

Provenance & Evidence