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

HRID 445827Notes

Reaction equation

HRID 445827 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-4a7819f2fad143acba8c5447a4cec35d
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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