Water → HCID 71291688, compound

Participants

Reaction Steps

1.54 g of sodium ethanolate (22.6 mmol), 4.00 g ethyl 3-(5-methylthiophen-2-yl)-3-oxopropanoate (2) and 6.67 g of ethyl bromoacetate are suspended under argon in absolute ethanol at 0° C. The mixture is stirred overnight. Water is added, ethanol is evaporated and the aqueous solution is extracted with diethyl ether. The organic phase is washed with water containing few drops of concentrated HCl, dried and evaporated to provide diethyl 2-(5-methylthiophene-2-carbonyl)succinate (3) which is used without further purification. A mixture of compound 3 and 11.64 g of ammonium acetate in glacial acetic acid is stirred at 120° C. under argon for 4 hours. After cooling to room temperature, the mixture is poured into water. The precipitate formed is isolated by filtration, washed with water and diethyl ether to provide compound 4. 1H NMR (300 MHz, CDCl3) δ 9.57 1H s, 7.61 1H d, 6.81 1H m, 4.24 2H q, 3.53 2H s, 2.54 3H large s, 1.31 3H t.

Provenance & Evidence