2-[(2,3-dimethylphenyl)methyl]oxirane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 1 (158 mg, 0.97 mmol), was dissolved in toluene (1.57 mL) and BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature. After 2 h at room temperature, a sample was mixed with solid NaHCO3, filtered, concentrated under reduced pressure, and the residue was analyzed by 1H NMR. The crude product consisted essentially of pure 2-(2,3-dimethylphenyl)propanal. BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature filtered concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 1 (158 mg, 0.97 mmol), was dissolved in toluene (1.57 mL) and BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature. After 2 h at room temperature, a sample was mixed with solid NaHCO3, filtered, concentrated under reduced pressure, and the residue was analyzed by 1H NMR. The crude product consisted essentially of pure 2-(2,3-dimethylphenyl)propanal. BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature filtered concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 4 (0.84 g, 5.18 mmol), was dissolved in dry dichloromethane (50 mL) and powdered Cu(BF4)2 hydrate (318 mg) was added at room temperature. After 2 h at room temperature, the mixture was washed with water, dried over Na2SO4 and concentrated under reduced pressure to yield 0.84 g (100%) of the title product. the mixture was washed with water dried over Na2SO4 concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A buffer was prepared by dissolving K2CO3 (20.7 g) and EDTA-Na2 (11.5 mg) in water (100 mL). 1,2-Dimethyl-3-(2-propenyl)benzene, compound of formula (XXIII), prepared according to example 3 (0.90 g, 6.16 mmol), was dissolved in a mixture of dichloromethane and acetonitrile (v/v 1:1, 60 mL), and the buffer prepared as described above (9.3 mL) was added. To the resulting mixture, first 1,1,1-trifluoroacetone (60 μL) and then hydrogen peroxide (30% in water, 6.2 mL, 60.7 mmol) were added and the mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water (100 mL), the organic phase was separated, and the aqueous phase was extracted with dichloromethane (2 times with 50 mL each). The combined organic phases were dried over Na2SO4, concentrated under reduced pressure, and the residue was purified by via silica gel column chromatography using hexane:ethyl acetate as eluent (v/v 32:1) to give 851 mg (85%) of the title compound. A buffer was prepared the buffer prepared was added the organic phase was separated the aqueous phase was extracted with dichloromethane (2 times with 50 mL each) The combined organic phases were dried over Na2SO4 concentrated under reduced pressure the residue was purified by via silica gel column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A buffer was prepared by dissolving K2CO3 (20.7 g) and EDTA-Na2 (11.5 mg) in water (100 mL). 1,2-Dimethyl-3-(2-propenyl)benzene, compound of formula (XXIII), prepared according to example 3 (0.90 g, 6.16 mmol), was dissolved in a mixture of dichloromethane and acetonitrile (v/v 1:1, 60 mL), and the buffer prepared as described above (9.3 mL) was added. To the resulting mixture, first 1,1,1-trifluoroacetone (60 μL) and then hydrogen peroxide (30% in water, 6.2 mL, 60.7 mmol) were added and the mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water (100 mL), the organic phase was separated, and the aqueous phase was extracted with dichloromethane (2 times with 50 mL each). The combined organic phases were dried over Na2SO4, concentrated under reduced pressure, and the residue was purified by via silica gel column chromatography using hexane:ethyl acetate as eluent (v/v 32:1) to give 851 mg (85%) of the title compound. A buffer was prepared the buffer prepared was added the organic phase was separated the aqueous phase was extracted with dichloromethane (2 times with 50 mL each) The combined organic phases were dried over Na2SO4 concentrated under reduced pressure the residue was purified by via silica gel column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 1 (158 mg, 0.97 mmol), was dissolved in toluene (1.57 mL) and BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature. After 2 h at room temperature, a sample was mixed with solid NaHCO3, filtered, concentrated under reduced pressure, and the residue was analyzed by 1H NMR. The crude product consisted essentially of pure 2-(2,3-dimethylphenyl)propanal. BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature filtered concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 1 (158 mg, 0.97 mmol), was dissolved in toluene (1.57 mL) and BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature. After 2 h at room temperature, a sample was mixed with solid NaHCO3, filtered, concentrated under reduced pressure, and the residue was analyzed by 1H NMR. The crude product consisted essentially of pure 2-(2,3-dimethylphenyl)propanal. BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature filtered concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 1 (158 mg, 0.97 mmol), was dissolved in toluene (1.57 mL) and BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature. After 2 h at room temperature, a sample was mixed with solid NaHCO3, filtered, concentrated under reduced pressure, and the residue was analyzed by 1H NMR. The crude product consisted essentially of pure 2-(2,3-dimethylphenyl)propanal. BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature filtered concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 4 (0.84 g, 5.18 mmol), was dissolved in dry dichloromethane (50 mL) and powdered Cu(BF4)2 hydrate (318 mg) was added at room temperature. After 2 h at room temperature, the mixture was washed with water, dried over Na2SO4 and concentrated under reduced pressure to yield 0.84 g (100%) of the title product. the mixture was washed with water dried over Na2SO4 concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A buffer was prepared by dissolving K2CO3 (20.7 g) and EDTA-Na2 (11.5 mg) in water (100 mL). 1,2-Dimethyl-3-(2-propenyl)benzene, compound of formula (XXIII), prepared according to example 3 (0.90 g, 6.16 mmol), was dissolved in a mixture of dichloromethane and acetonitrile (vv 1:1, 60 mL), and the buffer prepared as described above (9.3 mL) was added. To the resulting mixture, first 1,1,1-trifluoroacetone (60 μL) and then hydrogen peroxide (30% in water, 6.2 mL, 60.7 mmol) were added and the mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with water (100 mL), the organic phase was separated, and the aqueous phase was extracted with dichloromethane (2 times with 50 mL each). The combined organic phases were dried over Na2SO4, concentrated under reduced pressure, and the residue was purified by via silica gel column chromatography using hexane:ethyl acetate as eluent (vv 32:1) to give 851 mg (85%) of the title compound. A buffer was prepared the buffer prepared was added the organic phase was separated the aqueous phase was extracted with dichloromethane (2 times with 50 mL each) The combined organic phases were dried over Na2SO4 concentrated under reduced pressure the residue was purified by via silica gel column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 1 (158 mg, 0.97 mmol), was dissolved in toluene (1.57 mL) and BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature. After 2 h at room temperature, a sample was mixed with solid NaHCO3, filtered, concentrated under reduced pressure, and the residue was analyzed by 1H NMR. The crude product consisted essentially of pure 2-(2,3-dimethylphenyl)propanal. BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature filtered concentrated under reduced pressure

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 2-(2,3-Dimethylphenyl)methyloxirane, compound of formula (XXII), prepared according to example 1 (158 mg, 0.97 mmol), was dissolved in toluene (1.57 mL) and BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature. After 2 h at room temperature, a sample was mixed with solid NaHCO3, filtered, concentrated under reduced pressure, and the residue was analyzed by 1H NMR. The crude product consisted essentially of pure 2-(2,3-dimethylphenyl)propanal. BF3OEt2 (0.006 ml, 0.05 mmol) was added at room temperature filtered concentrated under reduced pressure