反应详情

A mixture of 4-(4-chlorophenyl)-3-butene-2-one (5.0 g), 1,3-cyclohexanedione (3.24 g), ammonium acetate (3.20 g) and 90 mL of ethanol were heated at reflux overnight and then cooled to room temperature. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and evaporated to obtain a yellow solid. Recrystallization from ethanol provided the title compound as a yellow solid (3.0 g); mp 201°-203° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.13-2.17 (m,2, CH2), 2.43-2.49 (m,2, CH2), 4.40 (d,1, J=4.9, CH), 4.60 (d,1, J=4.9, CH), 7.09-7.25 (m,4, Ar), 8.50 (s,1, NH); (CI, CH4) MS: m/z=274(M+1). Analysis for C16H16ClNO.0.15 H2O: Calculated: C, 69.51; H, 5.94; N, 5.07; Found: C, 69.47; H, 6.03; N, 4.91.

1. temperaturewere heated
2. temperatureat reflux overnight
3. customThe solvent was evaporated
4. customthe residue was partitioned between water and ethyl acetate
5. customThe organic layer was dried
6. filtrationfiltered
7. customevaporated
8. customto obtain a yellow solid
9. customRecrystallization from ethanol