Pyridine → 2-(alpha-Methoxycarbonyl-3,4-dimethoxybenzylidene)-1-methylpyrrolidine

HRID 1278034Notes

Reaction equation

HRID 1278034 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:17])[CH2:6][C:7]1[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[C:9]([O:10][CH3:11])[CH:8]=1)C.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CO>[CH3:2][O:4][C:5]([C:6](=[C:23]1[CH2:22][CH2:21][CH2:20][N:18]1[CH3:19])[C:7]1[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[C:9]([O:10][CH3:11])[CH:8]=1)=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 87441Ethyl 3,4-dimethoxyphenylacetateHCID 5360545Sodium

Product 1

HCID 544934312-(alpha-Methoxycarbonyl-3,4-dimethoxybenzylidene)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add a solution of 0.46 g of sodium in 5 ml of methanol dropwise to a mixture of 5.8 g of the title compound of Example 11 and 4.5 g of homoveratric acid ethyl ester in 15 ml of pyridine. Stir the resulting reaction mixture for 2 hours at 60°, and then distil pyridine and alcohol off under a vacuum before extracting the oily residue first with water and subsequently with petroleum ether. Chromatograph thus-extracted residue on a silica gel column with chloroform/methanol (19:1) to obtain eluate with an RF value 0.76. Concentrate the eluate to obtain a yield (10.5% of theory) of the title compound in the form of an oil.

Sources & evidence

ORD record
ord-f1bb17eb34e146dc8a5fe262154a0eb3
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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