2-pentylcyclopentan-1-one

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

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

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

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

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 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. 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 chromatography

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 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. 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 chromatography

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 270 mg (0.16 mmole) of Ru2Cl4 ((+)-BINAP)2 (NEt3), and 5 g (32 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 20 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 5 g (percent yield: 100%) of 2-pentylcyclopentanone as a clear yellow liquid. 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 chromatography

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 3-L reaction flask was charged with methylmagnesium chloride (MeMgCl) solution in tetrahydrofuran (THF) (800 mL, 2.4 mol) and THF (500 mL). The reaction flask was cooled to 5-10° C. 2-Pentyl-cyclopentanone (370 g, 2.4 mol) (prepared as above in EXAMPLE I) was fed into the reaction mixture over an hour. The reaction was aged for 4 hours and then neutralized with acetic acid (CH3COOH) (160 g) while the temperature was maintained at 5-10° C. The reaction mixture was poured into H2O (3 L) and toluene (1 L). The organic layer was separated and fractional distilled to afford 1-methyl-2-pentyl-cyclopentanol (245 g) having a boiling point of 150-152° C. at 3 mmHg. was maintained at 5-10° C The organic layer was separated fractional distilled

Conditions: temp:7.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 3-L reaction flask was charged with methylmagnesium chloride (MeMgCl) solution in tetrahydrofuran (THF) (800 mL, 2.4 mol) and THF (500 mL). The reaction flask was cooled to 5-10° C. 2-Pentyl-cyclopentanone (370 g, 2.4 mol) (prepared as above in EXAMPLE I) was fed into the reaction mixture over an hour. The reaction was aged for 4 hours and then neutralized with acetic acid (CH3COOH) (160 g) while the temperature was maintained at 5-10° C. The reaction mixture was poured into H2O (3 L) and toluene (1 L). The organic layer was separated and fractional distilled to afford 1-methyl-2-pentyl-cyclopentanol (245 g) having a boiling point of 150-152° C. at 3 mmHg. was maintained at 5-10° C The organic layer was separated fractional distilled

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

Procedure: A 3-L reaction flask was charged with cyclopentanone (500 g, 6 mol), water (H2O) (500 mL) and sodium hydroxide (NaOH) (10 g, 0.25 mol). Valeraldehyde (430 g, 5 mol) was fed into the reaction flask over 3 hours while the temperature was maintained at 25-30° C. After the feeding was completed, the reaction was aged for 2 hours and neutralized with hydrochloric acid (HCl) (30 g, 0.3 mol) while the temperature was maintained at 25-30° C. The reaction mass was further aged for 2 hours. The organic layer was separated and washed with saturated aqueous sodium bicarbonate (NaHCO3) (200 mL). The obtained crude product was fractionated to provide 2-pentylidene-cyclopentanone (523 g) having a boiling point of 122° C. at 3 mmHg A 1-L zipper autoclave was charged with 2-pentylidine cyclopentanone (523 g) and palladium on carbon (Pd/C) (2 g). The autoclave was purged three times with nitrogen followed by three times with hydrogen. The autoclave agitator was then turned on to 1500 rpm and the pressure was set to 100 psi. The reaction was allowed to exotherm to about 120° C. and maintained at this temperature for 2 hours. The autoclave was cooled to an ambient temperature. The hydrogen was then vented and the autoclave was subsequently purged three times with nitrogen. The Pd/C was removed by filtration through Celite®. The crude product 2-pentyl-cyclopentanone (520 g) was obtained and used in following steps without further purification. The autoclave was purged three times with nitrogen to exotherm to about 120° C. maintained at this temperature for 2 hours the autoclave was subsequently purged three times with nitrogen The Pd/C was removed by filtration through Celite®

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a three-necked 250 ml flask equipped with a magnetic stirrer and a reflux condenser were introduced 31 g of 2-pentyl cyclopentanone (0.2 mole), 31 g of anhydrous ethyl propionate, and 0.048 g (1 mol %) of anhydrous lithium hydroxide. The mixture was brought to reflux at ca. 100° C. Then 57.5 g (0.22 mole) of an anhydrous 13% w/w hydrogen peroxide solution in ethyl propionate, obtained from extraction of a 70% aqueous H2O2 solution by ethyl propionate, were slowly added over 4 h in the reactor while maintaining the reflux 2 h after the end of the introduction. The reaction mixture was then washed with 10% water to remove the non converted H202, and finally distilled to recover the solvent. In a three-necked 250 ml flask equipped with a magnetic stirrer and a reflux condenser