Triethylamine → 2-Pentylcyclohexan-1-one

HRID 1090488Notes

Reaction equation

HRID 1090488 reaction equation
CCN(CC)CC.[CH:8](=[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19])[CH2:9][CH2:10][CH2:11][CH3:12]>C(Cl)Cl>[CH2:8]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=[O:19])[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 1176002-Pentylidenecyclohexan-1-one

Product 1

HCID 1225472-Pentylcyclohexan-1-oneYield 95.1%

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 17.8 g (100 mmole) of 2-pentylidenecyclohexanone 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 23 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 16 g (percent yield: 90%) of 2-pentylcyclohexanone as a clear yellow liquid. 1H-NMR (CDCl3)δ(ppm): 1.20 (t, 3H, J=7 Hz), 1.40 (m, 8H), 1.50-2.50 (m, 9H)

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

Sources & evidence

ORD record
ord-189daca312054584a6455ac610d739e8
Source dataset
uspto-grants-1992_01
Patent number
US05081310

Reaction notes

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