Diethyl oxalacetate → Diethyl oxalacetate

HRID 268006Notes

Reaction equation

HRID 268006 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:17])[CH3:12].[CH2:24]([O:26][C:27](=[O:32])/[CH:28]=[C:29](\[NH2:31])/[CH3:30])C>C(O)C>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[CH2:11]([O:13][C:14](=[O:23])[CH2:15][C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:17])[CH3:12].[CH3:24][O:26][C:27](=[O:32])/[CH:28]=[C:29](\[NH2:31])/[CH3:30]

Participants

7

Reactant 3

HCID 66951Diethyl oxalacetateHCID 769854-(Methylthio)benzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 3

HCID 66951Diethyl oxalacetateHCID 769854-(Methylthio)benzaldehydeHCID 643918Methyl 3-aminocrotonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7.6 g of 4-methylmercaptobenzaldehyde, 9.5 g of oxalacetic acid diethyl ester and 6.5 g of β-aminocrotonic acid ethyl ester in 40 ccs of ethanol is heated to the boil overnight and evaporated in vacuo. Oil (orange). a. In the same way, 2-methyl-4-(4'-methylmercaptophenyl)-1,4-dihydropyridine-3-carboxylic acid methyl ester-5,6-dicarboxylic acid diethyl ester is obtained from 7.6 g of 4-methylmercaptobenzaldehyde, 9.5 g of oxalacetic acid diethyl ester and 5.8 g of β-aminocrotonic acid methyl ester.

Workup

  1. customevaporated in vacuo

Sources & evidence

ORD record
ord-c16c3b9ee4404985933d8eea99aa6006
Source dataset
uspto-grants-1976_03
Patent number
US03946027

Reaction notes

Loading…