2-[1-(2-hydroxyethyl)cyclohexyl]ethanol

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

Procedure: To a suspension of 60% sodium hydride/mineral oil (881 mg) in N,N-dimethylformamide (20 mL) was added 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (2.92 g) under ice cooling. To the solution was further added benzyl bromide (2.83 mL) under ice cooling, and it was stirred at room temperature for 63 hours. Water and 3N hydrochloric acid were added to the solution, and it was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4) to give the title compound (2.93 g). was extracted with ethyl acetate The organic layer was washed in turn with water and saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate concentrated under reduced pressure The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4)

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

Procedure: To a suspension of 60% sodium hydride/mineral oil (881 mg) in N,N-dimethylformamide (20 mL) was added 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (2.92 g) under ice cooling. To the solution was further added benzyl bromide (2.83 mL) under ice cooling, and it was stirred at room temperature for 63 hours. Water and 3N hydrochloric acid were added to the solution, and it was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4) to give the title compound (2.93 g). was extracted with ethyl acetate The organic layer was washed in turn with water and saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate concentrated under reduced pressure The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4)

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

Procedure: To a suspension of 60% sodium hydride/mineral oil (881 mg) in N,N-dimethylformamide (20 mL) was added 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (2.92 g) under ice cooling. To the solution was further added benzyl bromide (2.83 mL) under ice cooling, and it was stirred at room temperature for 63 hours. Water and 3N hydrochloric acid were added to the solution, and it was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4) to give the title compound (2.93 g). was extracted with ethyl acetate The organic layer was washed in turn with water and saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate concentrated under reduced pressure The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4)

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

Procedure: To a solution of 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (6.41 g) in dichloromethane (170 mL) were added triethylamine (6.74 mL) and tert-butyldiphenylchlorosilane (11.1 mL) at room temperature. After stirring the solution at room temperature for 18 hours, chloroform was added to the solution, and it was washed in turn with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The solution was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=85:15) to give the title compound (10.97 g). was washed in turn with 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution The solution was dried over anhydrous magnesium sulfate concentrated under reduced pressure The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=85:15)

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

Procedure: To a solution of 1,1,-cyclohexanediacetic acid (6.0 g) in tetrahydrofuran (90 mL) was added lithium aluminum hydride (2.28 g) under ice cooling. The solution was stirred under reflux for 4 hours, and then, cooled on ice, to which diethyl ether (200 mL), water (2.3 mL) and a 15% aqueous sodium hydroxide solution (2.3 mL) were added. After stirring the solution at room temperature for 30 minutes, water (6.9 mL) was added and the solution was stirred at room temperature for additional 30 minutes. Anhydrous magnesium sulfate was added to the solution, and it was filtered under reduced pressure. The filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, ethyl acetate) to give the title compound (4.83 g). under reflux for 4 hours After stirring the solution at room temperature for 30 minutes the solution was stirred at room temperature for additional 30 minutes was filtered under reduced pressure The filtrate was concentrated under reduced pressure The resulting residue was purified by chromatography (silica gel, ethyl acetate)

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

Procedure: To a solution of 1,1,-cyclohexanediacetic acid (6.0 g) in tetrahydrofuran (90 mL) was added lithium aluminum hydride (2.28 g) under ice cooling. The solution was stirred under reflux for 4 hours, and then, cooled on ice, to which diethyl ether (200 mL), water (2.3 mL) and a 15% aqueous sodium hydroxide solution (2.3 mL) were added. After stirring the solution at room temperature for 30 minutes, water (6.9 mL) was added and the solution was stirred at room temperature for additional 30 minutes. Anhydrous magnesium sulfate was added to the solution, and it was filtered under reduced pressure. The filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, ethyl acetate) to give the title compound (4.83 g). under reflux for 4 hours After stirring the solution at room temperature for 30 minutes the solution was stirred at room temperature for additional 30 minutes was filtered under reduced pressure The filtrate was concentrated under reduced pressure The resulting residue was purified by chromatography (silica gel, ethyl acetate)

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

Procedure: tert-Butylchlorodiphenylsilane (34.4 mL, 0.132 mol) was added dropwise to a solution of 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (21.7 g, 0.126 mol) in methylene chloride (280 mL) while cooling on ice. After stirring the mixture for 14 hours at room temperature, 25% aqueous ammonium chloride (300 mL) was added and extraction was performed. The organic layer was washed with saturated aqueous sodium chloride, and then the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (500 g Merck Art. 9385, hexane:ethyl acetate=4:1) to obtain the title compound as a colorless oil (36.8 g) (2 steps, 60% yield). while cooling on ice extraction The organic layer was washed with saturated aqueous sodium chloride the organic layer was dried over anhydrous magnesium sulfate filtered concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (500 g Merck Art. 9385, hexane:ethyl acetate=4:1)

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

Procedure: After suspending lithium aluminum hydride (11.4 g, 0.300 mol) in tetrahydrofuran (300 mL), a solution of 1,1-cyclohexanediacetic acid (30.0 g, 0.150 mol) in tetrahydrofuran (200 mL) was added dropwise at room temperature. After completion of the dropwise addition, the mixture was stirred for 5 minutes while cooling on ice, and then water (11.5 mL) was added dropwise over a period of 5 minutes while cooling on ice. After stirring for 10 minutes, 15% aqueous sodium hydroxide (11.5 mL) was added dropwise over a period of 5 minutes. Diethyl ether (500 mL, special grade) was added, and after stirring for 5 minutes, water (34.5 mL) was added. The mixture was then stirred for 2 hours while cooling on ice, and then celite was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and azeotropically distilled with toluene to obtain the title compound as a colorless oil (21.7 g). After completion of the dropwise addition while cooling on ice while cooling on ice After stirring for 10 minutes after stirring for 5 minutes The mixture was then stirred for 2 hours while cooling on ice celite was added the mixture was filtered The filtrate was concentrated under reduced pressure azeotropically distilled with toluene