4-Nitrobenzaldehyde → HCID 54192322, compound

HRID 2371962Notes

Reaction equation

HRID 2371962 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[CH:6]=[CH:7]/[CH2:8]P(OCC)(OCC)=O)=[O:5].[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)([O-:19])=[O:18].[H-].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[CH2:2]([O:3][C:4](=[O:5])[CH:6]=[CH:7][CH:8]=[CH:24][C:23]1[CH:26]=[CH:27][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=1)[CH3:1]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 24758Sodium hydrideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Product 1

HCID 54192322HCID 54192322, compound

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Triethyl 4-phosphonocrotonate is condensed with p-nitrobenzaldehyde in the presence of sodium hydride in toluene/tetrahydrofuran to yield 5-(p-nitrophenyl)-penta-2,4-dienoic acid ethyl ester, m.p. 150°-152°. Hydrogenation in ethyl acetate at one atmosphere pressure and room temperature using Adams catalyst yields ethyl 5-(4-amino-phenyl)-valerate. Condensation with acetonylacetone yields ethyl 5-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-valerate.

Sources & evidence

ORD record
ord-b689a06698094d22b2e318a7ae837e0d
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

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