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

HRID 482786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482786
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-37b3470a4d4f47938b25d97c9d4d8c96
Quelldatensatz
uspto-grants-1986_03
Patentnummer
US04575570

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