Water → 2-(2-Ethoxycarbonyl-acetylamino)-4-phenyl-thiophene-3-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

2-Amino-4-phenyl-thiophene-3-carboxylic acid ethyl ester (5.0 g, 0.02M) was dissolved in anhydrous dichloromethane (150 ml). Triethylamine (5.56 ml, 0.04M) was added and the mixture cooled to 0° C. Ethyl Malonyl Chloride (3.79 ml, 0.03M) was added over 5 min maintaining the temperature at 0° C. The reaction was then stirred at room temperature for 1 hr. Water (100 ml) was added and the organic layer separated. The aqueous layer was extracted with a further 100 ml of dichloromethane. The organics were combined, washed with water (2×100 ml) and dried over sodium sulphate. The concentrated residues were columned on silica, eluting with ethylacetate-cyclohexane 5-10% v/v. Pure fractions were combined and concentrated and the residues triturated with hexane, decanted and dried to give 2-(2-ethoxycarbonyl-acetylamino)-4-phenyl-thiophene-3-carboxylic acid ethyl ester as a white solid. Yield=6.95 g (96.2%).

Provenance & Evidence