Acetic Acid → Methyl 4-(3-chlorophenyl)-1,4-dihydro-2,6-dimethyl-5-phenylpyridine-3-carboxylate

反応式

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=O)[CH3:11])[CH:5]=[CH:6][CH:7]=1.[NH2:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23].C(O)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:10]([CH3:11])[NH:19][C:20]([CH3:26])=[C:21]2[C:22]([O:24][CH3:25])=[O:23])[CH:5]=[CH:6][CH:7]=1

参加物

実験手順

12.82 g (50 mmol) of 1-(3-chlorophenyl)-2-phenyl-3-oxo-1-butene in 80 ml of ethanol are heated to reflux with 11.5 g (100 mmol) of methyl β-aminocrotonate and 6 ml (100 mmol) of acetic acid overnight. 11.5 g of methyl β-aminocrotonate and 6 ml of acetic acid are added once more, and the mixture is heated under reflux for 24 hours. On cooling, crystals are produced, and these are filtered off with suction and washed with ethanol. For complete purification, they are passed through a silica gel column using toluene/ethyl acetate 20:1. 5.3 g of a colorless substance, of melting point 191° C., are obtained.