Ethyl 2-acetyl-3-(dimethylamino)acrylate

141-97-9

4637-24-5

134653-70-6

The general procedure for the synthesis of ethyl (Z)-2-((dimethylamino)methylene)-3-oxobutanoate from ethyl acetoacetate and N,N-dimethylformamide dimethyl acetal was as follows: referring to Example 75, ethyl acetoacetate (79 mL, 0.62 mol) was added to N,N-dimethylformamide dimethyl acetal (100 mL, 0.68 mol) and the mixture was heated to reflux for 1 hour. Upon completion of the reaction, the excess acetal was removed by subtractive distillation, followed by subtractive distillation of the residue to afford the target product (Z)-ethyl (Z)-2-((dimethylamino)methylene)-3-oxobutanoate (85 g, 74% yield). The boiling point of the product was 125-130 °C (400 Pa).1H-NMR (CDCl3) δ: 1.33 (3H, t, J = 7.1 Hz), 2.33 (3H, s), 3.04 (6H, br s), 4.23 (2H, q, J = 7.1 Hz), 7.68 (1H, s).