Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 46243463, compound

HRID 1773517Notes

Reaction equation

HRID 1773517 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[N+:11]([O-:13])=[O:12].C1(P(=[CH:33][C:34]([O:36][CH3:37])=[O:35])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:37][O:36][C:34](=[O:35])/[CH:33]=[CH:7]/[C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 7006084-Methoxy-3-nitrobenzaldehyde

Product 1

HCID 46243463HCID 46243463, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-methoxy-3-nitrobenzaldehyde (1.5 g, 8.2 mmol) and methyl (triphenylphosphoranylidene)acetate (4.4 g, 13 mmol) in tetrahydrofuran (30 mL) was heated at reflux overnight. The reaction mixture was cooled and evaporated under reduced pressure; the crude residue was purified by flash chromatography (acetone/hexane, 20/80) to afford 0.5 g of (E)-3-(4-methoxy-3-nitro-phenyl)-acrylic acid methyl ester.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. customevaporated under reduced pressure
  5. customthe crude residue was purified by flash chromatography (acetone/hexane, 20/80)

Sources & evidence

ORD record
ord-28f173eb839241eebb35c0634be7cd87
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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