(Triphenylphosphoranylidene)acetaldehyde → HCID 15596448, compound

HRID 1722223Notes

Reaction equation

HRID 1722223 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][CH2:10][CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:13]([CH:15]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:14]>C(Cl)Cl>[C:1]1([C:7]#[C:8][CH2:9][CH2:10]/[CH:11]=[CH:15]/[CH:13]=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 112406334-Pentynal, 5-phenyl-

Product 1

HCID 15596448HCID 15596448, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Phenylpent-4-ynal (0.5 g) in CH2Cl2 (5 ml) was added to a solution of formylmethylenetriphenyl phosphorane (1.8 g) in CH2Cl2 (10 ml) and the mixture was stirred at room temperature under a dry nitrogen atmosphere for 24 hours. The solvent was removed under reduced pressure and the residue was slurried with ether (50 m), filtered, and the residue washed with ether. The ethereal solutions were combined and the product was purified by chromatography on silica eluting with ether:hexane (1:9) to yield 7-phenylhept-2E-en-6-ynal (0.25 g) as a yellow oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. filtrationfiltered
  3. washthe residue washed with ether
  4. customthe product was purified by chromatography on silica eluting with ether:hexane (1:9)

Sources & evidence

ORD record
ord-868cb69a6d254feab5b398f27565b9ce
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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