Dimethyl benzylidenemalonate → 5-Ethoxycarbonyl-3-methoxycarbonyl-2-oxo-4-phenyl-6-propyl-1,2,3,4-tetrahydropyridine

HRID 1708149Notes

Reaction equation

HRID 1708149 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

Reactant 3

HCID 245906Dimethyl benzylidenemalonateHCID 2723922Sodium ethoxideHCID 85320704Ethyl 3-amino-hex-2-enoate

Product 1

HCID 233520795-Ethoxycarbonyl-3-methoxycarbonyl-2-oxo-4-phenyl-6-propyl-1,2,3,4-tetrahydropyridine

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.

Workup

  1. customThe mixture is chromatographed on silica gel
  2. customcrystallised from petroleum ether

Sources & evidence

ORD record
ord-9a8bce40277f4188aed0b6a0a97e0fa4
Source dataset
uspto-grants-1994_10
Patent number
US05356911

Reaction notes

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