Benzenepropanal → 3-Phenylprop-2-Enal

HRID 268012Notes

Reaction equation

HRID 268012 reaction equation
[CH:1](=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=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])[CH3:25]>C(O)C>[CH:1](=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=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])[CH3:25]

Participants

7

Reactant 3

HCID 7707BenzenepropanalHCID 66951Diethyl oxalacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 3

HCID 3073-Phenylprop-2-EnalHCID 66951Diethyl oxalacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13.4 g of hydrocinnamaldehyde, 19 g of oxalacetic acid diethyl ester and 13 g of β-aminocrotonic acid ethyl ester in 40 ccs of ethanol are heated to the boil for several hours and subsequently evaporated in vacuo. Oil (yelloworange). a) In the same manner, 13.2 g of cinnamaldehyde, 19 g of oxalacetic acid diethyl ester and 13 g of β-aminocrotonic acid ethyl ester in 40 ccs of ethanol yield 2-methyl-4-styrryl1,4-dihydropyridine-3,5,6-tricarboxylic acid triethyl ester as an oil.

Workup

  1. customsubsequently evaporated in vacuo

Sources & evidence

ORD record
ord-6455804215cb4f96831a45d1135a95f9
Source dataset
uspto-grants-1976_03
Patent number
US03946027

Reaction notes

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