Acetonitrile → 2-(2-Pentynyl)-2-cyclopenten-1-one

HRID 482786Notes

Reaction equation

HRID 482786 reaction equation
[CH2:1]([C:6]1(C(OCC=C)=O)[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])[C:2]#[C: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)[C:2]#[C:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 10868228Cyclopentanecarboxylic acid, 2-oxo-1-(2-pentynyl)-, 2-propenyl ester

Product 1

HCID 110080722-(2-Pentynyl)-2-cyclopenten-1-oneYield 85%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

A vessel was charged with 1 mole of allyl 1-(2-pentynyl)-2-oxocyclopentanecarboxylate of the following formula ##STR5## 20 moles of acetonitrile and 0.01 mole of palladium acetate. At room temperature, they were rapidly stirred. The mixture was then heated to the boiling point of the solvent, and the reaction was carried out under reflux for 30 minutes. After the reaction, the reaction mixture was distilled under reduced pressure in a customary manner to give 2-(2-pentynyl)-2-cyclopenten-1-one (PCP for short) in a yield of 85%. This compound was identified by using its IR, NMR and mass spectra.

Workup

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

Sources & evidence

ORD record
ord-37b3470a4d4f47938b25d97c9d4d8c96
Source dataset
uspto-grants-1986_03
Patent number
US04575570

Reaction notes

Loading…