Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86744573, compound

HRID 981146Notes

Reaction equation

HRID 981146 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)[CH3:2].[C:14]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:16][CH3:17])=[O:15]>C(#N)C>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]1[CH:11]=[CH:10][C:7](/[CH:8]=[CH:18]/[C:14]([O:16][CH3:17])=[O:15])=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 671144-(Diethylamino)benzaldehyde

Product 1

HCID 86744573HCID 86744573, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-(diethylamino) benzaldehyde (10 g) and carbomethoxymethylenetriphenylphosphorane (20 g) in dry acetonitrile (100 ml) was stirred at reflux under nitrogen for 24 h. The solvent was evaporated and the residual oil was treated with ER (100 ml). The precipitate was filtered, the filtrate was concentrated to an oil and the ER treatment was repeated. After filtration and evaporation the resulting orange oil was purified by [FCS] eluting with cyclohexane/EA/triethylamine 80:20:1) to give the title compound (10.0 g). T.l.c. (cyclohexane/EA/triethylamine 80:20:1) Rf 0.33.

Workup

  1. temperatureat reflux under nitrogen for 24 h
  2. customThe solvent was evaporated
  3. additionthe residual oil was treated with ER (100 ml)
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated to an oil
  6. filtrationAfter filtration and evaporation the resulting orange oil
  7. customwas purified by [FCS]
  8. washeluting with cyclohexane/EA/triethylamine 80:20:1)

Sources & evidence

ORD record
ord-d3f4d5cc436c4655a1cd3c5d881f5cdd
Source dataset
uspto-grants-1991_02
Patent number
US04990505

Reaction notes

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