(Triphenylphosphoranylidene)acetaldehyde → HCID 15596448, compound

HRID 2106861Notes

Reaction equation

HRID 2106861 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 ml), 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-705997d5e42841a5b2fa7ec5efb10efc
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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