(2-tert-butylphenyl)methanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1H, Ph-H), 7.41 (m, 1H, Ph-H), 7.24 (m, 2H, Ph-H), 4.93 (d, J=4.8 Hz, 2H, CH2OH), 1.54 (br, 1H, CH2OH), 1.43 (s, 1H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1 H, Ph-H), 7.41 (m, 1 H, Ph-H), 7.24 (m, 2 H, Ph-H), 4.93 (d, J=4.8 Hz, 2 H, CH2OH), 1.54 (br, 1 H, CH2OH), 1.43 (s, 1 H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1 H, Ph-H), 7.41 (m, 1 H, Ph-H), 7.24 (m, 2 H, Ph-H), 4.93 (d, J=4.8 Hz, 2 H, CH2OH), 1.54 (br, 1 H, CH2OH), 1.43 (s, 1 H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1H, Ph-H), 7.41 (m, 1H, Ph-H), 7.24 (m, 2H, Ph-H), 4.93 (d, J=4.8 Hz, 2H, CH2OH), 1.54 (br, 1H, CH2OH), 1.43 (s, 1H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1H, Ph-H), 7.41 (m, 1H, Ph-H), 7.24 (m, 2H, Ph-H), 4.93 (d, J=4.8 Hz, 2H, CH2OH), 1.54 (br, 1H, CH2OH), 1.43 (s, 1H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography

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

実験手順: To a solution of (2-tert-butylphenyl)methanol (935 mg) in DMSO (20 mL) were added triethylamine (4.81 mL) and sulfur trioxide pyridine complex (3.02 g). The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (780 mg). the mixture was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane)

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

実験手順: To a solution of 2-tert-butylbenzoic acid (1.00 g) in THF (20 mL) was added 1.0M borane THF complex THF solution (16.8 mL) under ice-cooling. The reaction mixture was stirred at room temperature overnight under a nitrogen atmosphere, 1N aqueous sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (942 mg). cooling the mixture was extracted with ethyl acetate The extract was dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane)

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1 H, Ph-H), 7.41 (m, 1 H, Ph-H), 7.24 (m, 2 H, Ph-H), 4.93 (d, J=4.8 Hz, 2 H, CH2OH), 1.54 (br, 1 H, CH2OH), 1.43 (s, 1 H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1 H, Ph-H), 7.41 (m, 1 H, Ph-H), 7.24 (m, 2 H, Ph-H), 4.93 (d, J=4.8 Hz, 2 H, CH2OH), 1.54 (br, 1 H, CH2OH), 1.43 (s, 1 H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography

反応条件: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-bromo-2-tert-butylbenzene (2.88 g, 13.51 mmol) in anhydrous THF (45 mL) 2,2′-dipyridyl (ca 10 mg) was added under a nitrogen atmosphere. The mixture was cooled down minus 78° C., and a solution of n-butyllithium (2.5 M in hexanes, 5.94 mL, 14.86 mmol) was added dropwise via syringe within the period of ten minutes. Upon addition, the mixture was stirred for 30 minutes, then warmed up to minus 30° C., and a flow of formaldehyde (generated from 1.91 g of paraformaldehyde by heating at over 160° C.) was passed through the solution until the deep red color disappeared completely. The mixture was quenched with saturated ammonium chloride solution (5 mL), then poured into a mixture of dichloromethane (100 mL) and water (50 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (20 mL) twice. The combined organic phase was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gel chromatography to yield 2-tert-butylbenzyl alcohol (1.67 g, 75%) as an oil. 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1H, Ph-H), 7.41 (m, 1H, Ph-H), 7.24 (m, 2H, Ph-H), 4.93 (d, J=4.8 Hz, 2H, CH2OH), 1.54 (br, 1H, CH2OH), 1.43 (s, 1H, C(CH3)3). Upon addition warmed up to minus 30° C. The mixture was quenched with saturated ammonium chloride solution (5 mL) poured into a mixture of dichloromethane (100 mL) and water (50 mL) The organic phase was separated the aqueous phase was extracted with dichloromethane (20 mL) twice The combined organic phase was dried over anhydrous Na2SO4 concentrated in vacuo purified by silica gel chromatography