1-methylcyclohexene

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

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

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

Procedure: A mixture of 20 ml trichlorosilane, 25 ml chloroform, 8.1 g 1-methylcyclohexene and 0.055 g (phenazine)PtCl2 (C2H4) was refluxed and stirred under nitrogen for 6 days. Distillation of the reaction mixture afforded 2.2 g of trichlorosilylmethylcyclohexane C6H11CH2SiCl3 which was characterized by its mass and NMR spectra. was refluxed Distillation of the reaction mixture

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

Procedure: A mixture of 20 ml trichlorosilane, 25 ml chloroform, 8.1 g 1-methylcyclohexene and 0.055 g (phenazine)PtCl2 (C2H4) was refluxed and stirred under nitrogen for 6 days. Distillation of the reaction mixture afforded 2.2 g of trichlorosilylmethylcyclohexane C6H11CH2SiCl3 which was characterized by its mass and NMR spectra. was refluxed Distillation of the reaction mixture

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

Procedure: In a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer were charged 7 ml of methylene chloride, 7 ml of water, 2 mmole of 1-methyl-1-cyclohexene, and 0.1 mmole of each of ruthenium catalysts shown in Table 2 below. To the mixture was added dropwise a 30% ethyl acetate solution of 1.52 g (6 mmole) of peracetic acid at room temperature over 2 hours while stirring on a magnetic stirrer. After the addition, the stirring was further continued at room temperature for 2 hours. The reaction mixture was extracted three times with 20 ml portions of methylene chloride. The extract was washed with 30 ml of a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residual crude product was purified by silica gel column chromatography using a 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent to obtain 2-methyl-2-hydroxy-1-cyclohexanone. The percent yield of the product is shown in Table 2. In a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer After the addition The reaction mixture was extracted three times with 20 ml portions of methylene chloride The extract was washed with 30 ml of a saturated sodium chloride aqueous solution dried over anhydrous magnesium sulfate The solvent was removed by distillation the residual crude product was purified by silica gel column chromatography a 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent

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

Procedure: In a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer were charged 7 ml of methylene chloride, 7 ml of water, 2 mmole of 1-methyl-1-cyclohexene, and 0.1 mmole of each of ruthenium catalysts shown in Table 2 below. To the mixture was added dropwise a 30% ethyl acetate solution of 1.52 g (6 mmole) of peracetic acid at room temperature over 2 hours while stirring on a magnetic stirrer. After the addition, the stirring was further continued at room temperature for 2 hours. The reaction mixture was extracted three times with 20 ml portions of methylene chloride. The extract was washed with 30 ml of a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residual crude product was purified by silica gel column chromatography using a 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent to obtain 2-methyl-2-hydroxy-1-cyclohexanone. The percent yield of the product is shown in Table 2. In a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer After the addition The reaction mixture was extracted three times with 20 ml portions of methylene chloride The extract was washed with 30 ml of a saturated sodium chloride aqueous solution dried over anhydrous magnesium sulfate The solvent was removed by distillation the residual crude product was purified by silica gel column chromatography a 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent

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

Procedure: Acetoxylation of 1-methylcyclohexene A 500 ml three-neck flask is charged with 15 g of 1-methylcyclohexene (0.15 moles), 150 g of acetic acid, 0.77 g of benzoquinone (7 mmoles), 1 g of active charcoal and 80 mg of palladium acetate (0.35 mmoles). The temperature is taken to 50°, then 8 g (0.17 moles) of 70% by weight hydrogen peroxide are introduced in 8 h, and the reaction is allowed to proceed for a further 2 h while maintaining the temperature at 50°. The acetic acid is then distilled (35°, 20×102Pa). The residue is distilled under vacuum (75°-80°, 15×102Pa) to provide 2-methyl-cyclohex-2-en-1-yl acetate (11 g, yield 50%). is taken to 50° while maintaining the temperature at 50° The acetic acid is then distilled (35°, 20×102Pa) The residue is distilled under vacuum (75°-80°, 15×102Pa)

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

Procedure: Acetoxylation of 1-methylcyclohexene A 500 ml three-neck flask is charged with 15 g of 1-methylcyclohexene (0.15 moles), 150 g of acetic acid, 0.77 g of benzoquinone (7 mmoles), 1 g of active charcoal and 80 mg of palladium acetate (0.35 mmoles). The temperature is taken to 50°, then 8 g (0.17 moles) of 70% by weight hydrogen peroxide are introduced in 8 h, and the reaction is allowed to proceed for a further 2 h while maintaining the temperature at 50°. The acetic acid is then distilled (35°, 20×102Pa). The residue is distilled under vacuum (75°-80°, 15×102Pa) to provide 2-methyl-cyclohex-2-en-1-yl acetate (11 g, yield 50%). is taken to 50° while maintaining the temperature at 50° The acetic acid is then distilled (35°, 20×102Pa) The residue is distilled under vacuum (75°-80°, 15×102Pa)

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the procedure of Spurr et al, J. Am. Chem. Soc., 1983, 105, 4735, a solution of 1-methyl-1-cyclohexene (1 g, 10.4 mmol) in dichloromethane (30 mL) was cooled to −20° C. and chlorosulfonylisocyanate (1.08 mL, 12.5 mmol) was added drop wise. The reaction was warmed to −10° C. over 3 h, then warmed to room temperature and stirred for 1 h. The reaction mixture was then concentrated, and taken up in ether (15 mL) and dimethylethyleneglycol (5 mL) to homogenize. To the reaction mixture was added 25% Na2SO3 (25 mL), followed by 10% sodium hydroxide solution to keep the pH between 7-8. The reaction was stirred overnight, taken up in ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated to afford racemic (1S,6R)-6-methyl-7-azabicyclo[4.2.0]octan-8-one (0.95 g, 66%). MS: 140.1 (M+H)+ warmed to room temperature The reaction mixture was then concentrated dimethylethyleneglycol (5 mL) to homogenize To the reaction mixture was added 25% Na2SO3 (25 mL) The reaction was stirred overnight washed with brine dried over MgSO4 filtered concentrated

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

Procedure: To a solution of 2-(4-methylphenyl)benzofuran-5-carbaldehyde (500 mg) and 1-methylcyclohexene (1.2 ml) in DMF (15 ml) was added a solution (9 ml) of sodium chlorite (80%, 1.5 g) and sodium dihydrogenphosphate (1.5 g) at room temperature, and the mixture was stirred for 3 hours. To the mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with sodium thiosulfate and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the precipitated crystals were collected by filtration, which were washed with diethylether to give colorless crystals of 2-(4-methylphenyl)benzofuran-5-carboxylic acid (395 mg). the mixture was extracted with ethyl acetate The organic layer was washed with sodium thiosulfate and saturated brine dried with magnesium sulfate Under reduced pressure, the mixture was concentrated the precipitated crystals were collected by filtration, which were washed with diethylether

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

Procedure: A mixture of 20 ml trichlorosilane, 25 ml chloroform, 8.1 g 1-methylcyclohexene and 0.055 g (phenazine)PtCl2 (C2H4) was refluxed and stirred under nitrogen for 6 days. Distillation of the reaction mixture afforded 2.2 g of trichlorosilylmethylcyclohexane C6H11CH2SiCl3 which was characterized by its mass and NMR spectra. was refluxed Distillation of the reaction mixture

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

Procedure: In a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer were charged 7 ml of methylene chloride, 7 ml of water, 2 mmole of 1-methyl-1-cyclohexene, and 0.1 mmole of each of ruthenium catalysts shown in Table 2 below. To the mixture was added dropwise a 30% ethyl acetate solution of 1.52 g (6 mmole) of peracetic acid at room temperature over 2 hours while stirring on a magnetic stirrer. After the addition, the stirring was further continued at room temperature for 2 hours. The reaction mixture was extracted three times with 20 ml portions of methylene chloride. The extract was washed with 30 ml of a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residual crude product was purified by silica gel column chromatography using a 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent to obtain 2-methyl-2-hydroxy-1-cyclohexanone. The percent yield of the product is shown in Table 2. In a 50 ml flask equipped with a thermometer, a dropping funnel, and a stirrer After the addition The reaction mixture was extracted three times with 20 ml portions of methylene chloride The extract was washed with 30 ml of a saturated sodium chloride aqueous solution dried over anhydrous magnesium sulfate The solvent was removed by distillation the residual crude product was purified by silica gel column chromatography a 5:1 (by volume) mixture of n-hexane and ethyl acetate as an eluent