2-Pentylidenecyclopentanone → 2-Pentylcyclopentan-1-one

HRID 1090486Notes

Reaction equation

HRID 1090486 reaction equation
[CH:1](=[C:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5]>C(Cl)Cl>[CH2:1]([CH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 1

HCID 860002-Pentylidenecyclopentanone

Product 1

HCID 209592-Pentylcyclopentan-1-oneYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

In a 100 ml-volume three-way-cocked eggplant type flask whose atmosphere had been displaced with nitrogen was charged 735 mg (0.66 mmole) of [RuI(p-cymene)((+]-BINAP)]I, and 2.5 g (16 mmole) of 2-pentylidenecyclopentanone and 50 ml of methylene chloride were added thereto to form a solution. The solution was put in a 100 ml autoclave having been displaced with nitrogen and stirred at 50° C. under a hydrogen pressure of 60 kg/cm2 for 113 hours to conduct a hydrogenation reaction. The solvent was removed from the reaction mixture by distillation, and the residue was purified by silica gel column chromatography using a mixed solvent of diethyl ether and hexane (1:4 by volume) as an eluent to obtain 1.7 g (percent yield 67%) of 2-pentylcyclopentanone.

Workup

  1. additionwere added
  2. customto form a solution
  3. customa hydrogenation reaction
  4. customThe solvent was removed from the reaction mixture by distillation
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99d9a8ab1bce48e48824068c55298f8d
Source dataset
uspto-grants-1992_01
Patent number
US05081310

Reaction notes

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