Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 10656958, compound

HRID 2106856Notes

Reaction equation

HRID 2106856 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.[C:13]([CH:18]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:15][CH2:16][CH3:17])=[O:14]>C(Cl)Cl>[C:1]1([C:7]#[C:8][CH2:9][CH2:10]/[CH:11]=[CH:18]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 112406334-Pentynal, 5-phenyl-

Product 1

HCID 10656958HCID 10656958, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Phenylpent-4-ynal (3 g) in dry CH2Cl2 (30 ml) was added to a solution of carbethoxymethylenetriphenylphosphorane (10 g) in dry dichloromethane (20 ml), and the mixture was heated at reflux under a nitrogen atmosphere for 5 hours. The solvent was removed under reduced pressure, and the product was purified by chromatography on silica (150 g), eluting with 2:1 hexane:ether to yield ethyl 7-phenylhept-2E-en-6-ynoate (3.6 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 5 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe product was purified by chromatography on silica (150 g)
  5. washeluting with 2:1 hexane

Sources & evidence

ORD record
ord-d3dbf0ebf91d4bd69543ef058412cd92
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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