Dimethyl benzylidenemalonate → 5-Ethoxycarbonyl-3-methoxycarbonyl-2-oxo-4-phenyl-6-propyl-1,2,3,4-tetrahydropyridine
Reaction equation
[CH:1](=[C:8]([C:13]([O:15]C)=O)[C:9]([O:11][CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:27])[CH:21]=[C:22]([NH2:26])[CH2:23][CH2:24][CH3:25])[CH3:18].[O-]CC.[Na+]>>[CH2:17]([O:19][C:20]([C:21]1[CH:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:8]([C:9]([O:11][CH3:12])=[O:10])[C:13](=[O:15])[NH:26][C:22]=1[CH2:23][CH2:24][CH3:25])=[O:27])[CH3:18]Participants
4
Procedure
26.2 g (0.128 mol) of dimethyl benzylidenemalonate and 20.1 g (0.128 mol) of ethyl-3-amino-hex-2-en-oate are stirred at 140° C. for 3 days with a spatula tip full of sodium ethoxide. The mixture is chromatographed on silica gel using methylene chloride and crystallised from petroleum ether.