Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 23112249, compound

HRID 2264321Notes

Reaction equation

HRID 2264321 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15])=O.C1(P(=[CH:36][C:37]([O:39][CH3:40])=[O:38])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:40][O:39][C:37](=[O:38])/[CH:36]=[CH:1]/[C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 18001104Ethyl 4-formyl-3-nitrobenzoate

Product 1

HCID 23112249HCID 23112249, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 70 ml of toluene was dissolved 3.2 g of ethyl 4-formyl-3-nitrobenzoate and then 5.75 g of methyl triphenylphosphoranylideneacetate, followed by 6 hours of stirring under reflux. After cooling, the reaction solution was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 3.63 g of ethyl 4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-3-nitrobenzoate as a white solid.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2a363dfce50e48f398327e36bcfb31e4
Source dataset
uspto-grants-2010_12
Patent number
US07855198B2

Reaction notes

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