2-(1-benzofuran-2-yl)propan-2-ol

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

Procedure: 3.10 g of 2-(1-hydroxy-1-methylethyl)benzofuran was dissolved in 100 ml of methylene chloride. Thereto were added 2.22 g of methanesulfonyl chloride and 3.92 g of triethylamine at 0° C. The mixture was stirred at room temperature for 4 hours, then washed with water, 1 N hydrochloric acid, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene) to obtain 2.44 g (yield: 88%) of 2-isopropenylbenzofuran as a colorless oily material. washed with water, 1 N hydrochloric acid an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure The residue was purified by column chromatography (eluant: toluene)

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

Procedure: 1.00 g of benzofuran was dissolved in 20 ml of anhydrous tetrahdyrofuran. Thereto was dropwise added 6.2 ml of 1.5 M n-butyllithium hexane solution, in 5 minutes with stirring at -50° C. The mixture was stirred at 0° C. for 30 minutes and then cooled to -50° C. Thereto was added 0.94 ml of acetone. The resulting mixture was stirred at room temperature for 30 minutes. The solvent was removed by distillation under reduced pressure. The residue was mixed with 30 ml of chloroform and 10 ml of water to dissolve the residue. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 1.50 g of 2-(1-hydroxy-1-methylethyl)benzofuran as a colorless oily material. The mixture was stirred at 0° C. for 30 minutes cooled to -50° C The resulting mixture was stirred at room temperature for 30 minutes The solvent was removed by distillation under reduced pressure The residue was mixed with 30 ml of chloroform and 10 ml of water to dissolve the residue The organic layer was separated washed with an aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure

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

Procedure: 3.10 g of 2-(1-hydroxy-1-methylethyl)benzofuran was dissolved in 100 ml of methylene chloride. Thereto were added 2.22 g of methanesulfonyl chloride and 3.92 g of triethylamine at 0° C. The mixture was stirred at room temperature for 4 hours, then washed with water, 1 N hydrochloric acid, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene) to obtain 2.44 g (yield: 88%) of 2-isopropenylbenzofuran as a colorless oily material. washed with water, 1 N hydrochloric acid an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure The residue was purified by column chromatography (eluant: toluene)

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

Procedure: 1.00 g of benzofuran was dissolved in 20 ml of anhydrous tetrahdyrofuran. Thereto was dropwise added 6.2 ml of 1.5 M n-butyllithium hexane solution, in 5 minutes with stirring at -50° C. The mixture was stirred at 0° C. for 30 minutes and then cooled to -50° C. Thereto was added 0.94 ml of acetone. The resulting mixture was stirred at room temperature for 30 minutes. The solvent was removed by distillation under reduced pressure. The residue was mixed with 30 ml of chloroform and 10 ml of water to dissolve the residue. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 1.50 g of 2-(1-hydroxy-1-methylethyl)benzofuran as a colorless oily material. The mixture was stirred at 0° C. for 30 minutes cooled to -50° C The resulting mixture was stirred at room temperature for 30 minutes The solvent was removed by distillation under reduced pressure The residue was mixed with 30 ml of chloroform and 10 ml of water to dissolve the residue The organic layer was separated washed with an aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure

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

Procedure: Into 200 ml of ethanol, was dissolved 10.3 g of 2-(1-methyl-1-hydroxyethyl)benzofuran. To the solution, was added 1.1 g of 10% palladium carbon. Hydrogen was introduced into the mixture with shaking at atmospheric pressure and at room temperature until no more hydrogen had been absorbed (it took 6 hours). The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was distilled under reduced pressure to obtain 6.86 g of the intended product boiling at 78°-95° C./0.4 mmHg. had been absorbed (it took 6 hours) The reaction mixture was filtered the filtrate was concentrated in vacuo The residue was distilled under reduced pressure

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

Procedure: 3.10 g of 2-(1-hydroxy-1-methylethyl)benzofuran was dissolved in 100 ml of methylene chloride. Thereto were added 2.22 g of methanesulfonyl chloride and 3.92 g of triethylamine at 0° C. The mixture was stirred at room temperature for 4 hours, then washed with water, 1 N hydrochloric acid, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene) to obtain 2.44 g (yield: 88%) of 2-isopropenylbenzofuran as a colorless oily material. washed with water, 1 N hydrochloric acid an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution in this order, and dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure The residue was purified by column chromatography (eluant: toluene)

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

Procedure: 1.00 g of benzofuran was dissolved in 20 ml of anhydrous tetrahdyrofuran. Thereto was dropwise added 6.2 ml of 1.5 M n-butyllithium hexane solution, in 5 minutes with stirring at -50° C. The mixture was stirred at 0° C. for 30 minutes and then cooled to -50° C. Thereto was added 0.94 ml of acetone. The resulting mixture was stirred at room temperature for 30 minutes. The solvent was removed by distillation under reduced pressure. The residue was mixed with 30 ml of chloroform and 10 ml of water to dissolve the residue. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 1.50 g of 2-(1-hydroxy-1-methylethyl)benzofuran as a colorless oily material. The mixture was stirred at 0° C. for 30 minutes cooled to -50° C The resulting mixture was stirred at room temperature for 30 minutes The solvent was removed by distillation under reduced pressure The residue was mixed with 30 ml of chloroform and 10 ml of water to dissolve the residue The organic layer was separated washed with an aqueous saturated sodium chloride solution dried over anhydrous magnesium sulfate The solvent was removed by distillation under reduced pressure