2-pentylidenecyclohexan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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) were added to form a solution a hydrogenation reaction The solvent was removed from the reaction mixture by distillation the residue was purified by silica gel column

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

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) were added to form a solution a hydrogenation reaction The solvent was removed from the reaction mixture by distillation the residue was purified by silica gel column