Acetamidomalonic acid diethyl ester → HCID 86753717, compound

Participants

Reaction Steps

4.37 g (190 mmol) of sodium metal were dissolved in 110 ml of anhydrous ethanol. 41.14 g (189.6 mmol) of diethyl acetamidomalonate dissolved in 270 ml of anhydrous ethanol were added and the mixture was heated under reflux for 10 minutes. 25.65 g (168 mmol) of (Z)-1-bromo-2-butene were added dropwise at room temperature and the mixture was stirred overnight, then evaporated to dryness under vacuum and the residue was partitioned between ethyl acetate and 0.1 M hydrochloric acid. The organic phase was washed with saturated sodium hydrogen carbonate solution followed by saturated sodium chloride solution and dried over anhydrous magnesium sulphate. After removal of the solvent by evaporation the crude product was chromatographed on silica gel using 66% ethyl acetate in petroleum ether as eluent to obtain 44.69 g of diethyl (Z)-2-acetamido-2-(2-butenyl)malonate as a colourless oil;1H NMR (250 MHz, CDCl3) δ: 1.2 (t, 6H), 1.6 (d, 3H), 2.0 (s, 3H), 3.1 (d, 2H), 4.2 (q, 4H), 5.1(m, 1H), 5.6 (m, 1H), 6.7 (s, 1H).

Provenance & Evidence