Acetonitrile → 2-Pentylidenecyclopentanone

HRID 2413370Notes

Reaction equation

HRID 2413370 reaction equation
[CH2:1]([C:6]1(C(OCC=C)=O)[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5].C(#N)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([C:6]1[C:7](=[O:11])[CH2:8][CH2:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:1](=[C:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 13005779Prop-2-en-1-yl 2-oxo-1-pentylcyclopentane-1-carboxylate

Product 2

HCID 860002-PentylidenecyclopentanoneHCID 1175492-Cyclopenten-1-one, 2-pentyl-

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A vessel was charged with 1 mole of allyl 1-pentyl-2-oxocyclopentanecarboxylate of the following formula ##STR7## 20 moles of acetonitrile, 0.05 mole of palladium acetate and 0.05 mole of α,β-ethylenedi(diphenyl)phosphine, and after these materials were rapidly stirred at room temperature, they were heated to the boiling point of the solvent and reacted under reflux for 30 minutes. After the reaction, the reaction mixture was distilled under reduced pressure in a customary manner to give 2-pentyl-2-cyclopenten-1-one and 2-pentylidenecyclopentanone in a yield of 65% and 13%, respectively. These compounds were identified by using IR, NMR and mass spectroscopic techniques.

Workup

  1. temperaturethey were heated to the boiling point of the solvent
  2. customreacted
  3. temperatureunder reflux for 30 minutes
  4. customAfter the reaction
  5. distillationthe reaction mixture was distilled under reduced pressure in a customary manner

Sources & evidence

ORD record
ord-b9569292ecad4adab38cf33cd131a0a1
Source dataset
uspto-grants-1985_01
Patent number
US04496766

Reaction notes

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