(Triphenylphosphoranylidene)acetaldehyde → Triphenylphosphine Oxide

HRID 1195360Notes

Reaction equation

HRID 1195360 reaction equation
FC1C=CC(C(C2C=CC(F)=CC=2)=C(C2N(C)N=NN=2)C=[O:11])=CC=1.[C:25]1([P:31](=CC=O)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1C=CC=CC=1>[C:25]1([P:31](=[O:11])([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 14539527HCID 14539527, compound

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 3,3-bis(4-fluorophenyl)-2-(1-methyl-1H-tetrazol-5-yl)-2-propenal (71.6 g, 0.22 mole) and triphenylphosphoranylidene acetaldehyde (66.8 g, 0.22 mole) was added 1.1 liters of dry benzene and the suspension was heated to reflux temperature over a period of 30 minutes. The reaction was allowed to proceed at reflux temperature for 2 hours. Analytical TLC eluted five times with 30% (v/v) ethyl acetate in hexanes showed only one major spot at Rf =0.37 for the desired product. The crude hot reaction mixture was diluted with an equal volume of hexane and the warm mixture was quickly filtered through a bed of activated charcoal. The filtrate was allowed to stand at room temperature from which 58.12 g (75.2%) of the desired product was collected. A second crystallization from the filtrate yielded mostly triphenylphosphine oxide. Concentration of the filtrate yielded an additional amount of the desired product to give a total of 71 g (91.8%) of the title compound. The combined material was recrystallized from ethyl acetate-hexane to give pure title compound; m.p.=164°-165° C. A 1H NMR of the recrystallized material showed no detectable double homologated product.

Workup

  1. temperaturethe suspension was heated
  2. temperatureto reflux temperature over a period of 30 minutes
  3. temperatureat reflux temperature for 2 hours
  4. washAnalytical TLC eluted five times with 30% (v/v) ethyl acetate in hexanes
  5. additionThe crude hot reaction mixture was diluted with an equal volume of hexane
  6. filtrationthe warm mixture was quickly filtered through a bed of activated charcoal
  7. customto stand at room temperature from which 58.12 g (75.2%) of the desired product
  8. customwas collected
  9. customA second crystallization from the filtrate

Sources & evidence

ORD record
ord-ef839ed8edc0442f8d4edca0e886f960
Source dataset
uspto-grants-1992_05
Patent number
US05110940

Reaction notes

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