4-Nitrobenzaldehyde → Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoate

HRID 1876385Notes

Reaction equation

HRID 1876385 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12]([O:14][C:15]([C:17](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:18])=[O:16])[CH3:13]>O1CCCC1>[CH3:18]/[C:17](=[CH:8]\[C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)/[C:15]([O:14][CH2:12][CH3:13])=[O:16]

Participants

4

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionate

Product 1

HCID 11241815Ethyl (E)-2-methyl-3-(4-nitrophenyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzaldehyde (2 g, 13.2 mmol) and (1-ethoxy carbonylethylidene)triphenyl phosphorane (4.80 g, 13.2 mmol) in tetrahydrofuran (130 mL) was refluxed for 24 hours. The reaction was concentrated in vacuo and was purified by flash column chromatography on silica gel with hexanes and EtOAc to give (E)-ethyl 2-methyl-3-(4-nitrophenyl)acrylate (645).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customwas purified by flash column chromatography on silica gel with hexanes and EtOAc

Sources & evidence

ORD record
ord-477abf0fce6a4070a0ba3105fe1404e6
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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