Triethylamine → 2-Pentylcyclopentan-1-one

HRID 1090485Notes

Reaction equation

HRID 1090485 reaction equation
CCN(CC)CC.[CH:8](=[C:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])[CH2:9][CH2:10][CH2:11][CH3:12]>CO>[CH2:8]([CH:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[O:18])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 860002-Pentylidenecyclopentanone

Product 1

HCID 209592-Pentylcyclopentan-1-oneYield 93.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 230 mg (0.14 mmole) of Ru2Cl4 ((+)-BINAP)2 (NEt3), and 5 g (32 mmole) of 2-pentylidenecyclopentanone and 50 ml of methanol 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 90 kg/cm2 for 110 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 4.6 g (percent yield: 92%) 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-c0d41b92f4ac4beaad058830ace285e0
Source dataset
uspto-grants-1992_01
Patent number
US05081310

Reaction notes

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