3-(2-Pyridyl)-2-cyclopenten-1-one → 3-(2-Pyridyl)cyclopentan-1-one

HRID 655137Notes

Reaction equation

HRID 655137 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH2:11][CH2:10][C:9](=[O:12])[CH:8]=1>CCO.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8]1

Participants

4

Reactant 1

HCID 392355473-(2-Pyridyl)-2-cyclopenten-1-one

Product 1

HCID 594861153-(2-Pyridyl)cyclopentan-1-oneYield 225.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(2-pyridyl)-2-cyclopenten-1-one (1.43 g, 8.98 mmol) and 10% Pd/C (142 mg) in EtOH (30 mL) was stirred under hydrogen atmosphere (0.3 MPa) for 6.5 h. The catalyst was removed by filtration over Celite and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (Hexane/EtOAc=1/1) to yield 3-(2-pyridyl)cyclopentan-1-one (3.26 g, 94%) as colorless oil.

Workup

  1. customThe catalyst was removed by filtration over Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by column chromatography (Hexane/EtOAc=1/1)

Sources & evidence

ORD record
ord-68742832c65740f2be7f38b4ca104c31
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

Loading…