Methyl acetoacetate → HCID 23319388, compound

Participants

Reaction Steps

To a 250 ml round bottomed flask was added the compound (2c) (5.70 g, 22.90 mmol), methyl acetoacetate (2.66 g, 22.90 mmol), methyl 3-aminocrotonate (2.64 g, 22.90 mmol) and 2-propanol (30 ml). The flask was equipped with a stirring bar, reflux condenser and argon inlet and the mixture was heated at reflux for 20 hours with stirring. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The crude product was chromatographed on 300 g of silica gel using 1:3 ethyl acetate-hexanes as eluant. The yellow oil obtained from the chromatography was triturated with ethyl ether and the resulting crystals of pure compound (2d) were collected on a first and dried. mp 156-158° C. 'H NMR (CDCl3) δ2.26 (s, 6H), 3.50 (s, 6H), 4.69 (s, 2H), 4.95 (s 2H), 5.00 (s, 1H), 5.95 (br s, 1H), 7.00-7.60 (m, 8H).

Provenance & Evidence