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

HRID 1909542Notes

Reaction equation

HRID 1909542 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-fa3292f0e2cb48ff8976d07d1de45291
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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