Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 14196833, compound

HRID 2232741Notes

Reaction equation

HRID 2232741 reaction equation
[C:1]1([C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][CH:9]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[CH2:20]([O:19][C:17](=[O:18])/[CH:22]=[CH:9]\[CH:8]=[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:21]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 710273,3-Diphenylacrolein

Product 1

HCID 14196833HCID 14196833, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3,3-diphenyl-2-propenal (18.73 g) and (carbethoxymethylene)triphenylphosphorane (33.1 g) in ethanol (100 mL) was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the residual solid was refluxed in a mixture of ether (125 mL) and hexane (250 mL) for 10 minutes. The mixture was cooled to room temperature and the precipitated triphenylphosphine oxide (25 g) was removed by filtration and was washed with ether-hexane (1:2; 2×50 mL). The filtrates were evaporated and the residue was passed through a short column of silica gel (200 g) made up in dichloromethane to remove residual triphenylphosphine oxide and starting ylid. After evaporation of the appropriate eluates, the resulting mixture of esters was separated by using HPLC (dichloromethane-hexane; 1:1). The fractions containing the less polar material were combined and evaporated to yield 4.2 g of (Z)-5,5-diphenyl-2,4-pentadienoic acid ethyl ester as an oil which crystallized on standing, mp 36°-37° C.

Workup

  1. customThe solvent was removed in vacuo
  2. temperaturethe residual solid was refluxed in a mixture of ether (125 mL) and hexane (250 mL) for 10 minutes
  3. customthe precipitated triphenylphosphine oxide (25 g) was removed by filtration
  4. washwas washed with ether-hexane (1:2; 2×50 mL)
  5. customThe filtrates were evaporated
  6. customto remove residual triphenylphosphine oxide
  7. customAfter evaporation of the appropriate eluates
  8. additionthe resulting mixture of esters
  9. customwas separated
  10. additionThe fractions containing the less polar material
  11. customevaporated

Sources & evidence

ORD record
ord-c18e1b09f8c24899abce812ce96dd8dd
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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