Triethylamine → 2-propylcyclopentanone

HRID 1090487Notes

Reaction equation

HRID 1090487 reaction equation
CCN(CC)CC.[CH:8](=[C:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])[CH2:9][CH3:10]>C(Cl)Cl>[CH2:8]([CH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 30161952-Propylidenecyclopentanone

Product 1

HCID 5184612-propylcyclopentanoneYield 97%

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 845 mg (0.5 mmole) of Ru2Cl4 ((+)-BINAP)2 (NEt3), and 12.4 g (100 mmole) of 2-propylidenecyclopentanone 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 90 kg/cm2 for 28 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 12 g (percent yield: 97%) of 2-propylcyclopentanone as a clear yellow liquid. 1H-NMR (CDCl3)δ(ppm): 1.50 (t, 3H, J=7 Hz), 1.42 (m, 4H), 1.50-2.80 (m, 7H)

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-98705cdbabc04c87bacb3de4a960f407
Source dataset
uspto-grants-1992_01
Patent number
US05081310

Reaction notes

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