(1-prop-2-enylcyclohexyl)methanol

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

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

Procedure: To a solution of (1-allylcyclohexyl)methanol (1.0 g) in N,N-dimethylformamide (7 mL) were added imidazole (661 mg) and triethylchlorosilane (1.41 mL) at room temperature. After stirring the solution at room temperature for 3 hours, N,N-dimethylformamide was added thereto and it was extracted with hexane. The combined hexane layer was washed with acetonitrile and concentrated under reduced pressure to give the title compound (1.70 g). This product was subjected to the subsequent step without further purification. it was extracted with hexane The combined hexane layer was washed with acetonitrile concentrated under reduced pressure

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

Procedure: To a solution of cyclohexane carbaldehyde (2.24 g) in N,N-dimethylformamide (30 mL) were added potassium tert-butoxide (2.70 g) and allyl bromide (4.33 mL) under ice cooling. The solution was stirred under ice cooling for 30 minutes. Water and 1N hydrochloric acid were then added to the solution, and it was extracted with diethyl ether. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To a solution of the resulting residue in ethanol (60 mL) was added sodium borohydride (567 mg) under ice cooling. The solution was stirred at room temperature for 16 hours. Acetic acid was added to the solution, and it was concentrated under reduced pressure. To the resulting residue was added saturated aqueous sodium bicarbonate solution, and it was extracted with diethyl ether. 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 column chromatography (silica gel, hexane:ethyl acetate=4:1) to give the title compound (1.47 g). was extracted with diethyl ether The organic layer was washed with water and saturated aqueous sodium chloride solution dried over anhydrous magnesium sulfate concentrated under reduced pressure To a solution of the resulting residue in ethanol (60 mL) was added sodium borohydride (567 mg) under ice cooling The solution was stirred at room temperature for 16 hours Acetic acid was added to the solution, and it was concentrated under reduced pressure To the resulting residue was added saturated aqueous sodium bicarbonate solution, and it was extracted with diethyl ether 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 column chromatography (silica gel, hexane:ethyl acetate=4:1)

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

Procedure: To a solution of (1-allylcyclohexyl)methanol (1.0 g) in N,N-dimethylformamide (7 mL) were added imidazole (661 mg) and triethylchlorosilane (1.41 mL) at room temperature. After stirring the solution at room temperature for 3 hours, N,N-dimethylformamide was added thereto and it was extracted with hexane. The combined hexane layer was washed with acetonitrile and concentrated under reduced pressure to give the title compound (1.70 g). This product was subjected to the subsequent step without further purification. it was extracted with hexane The combined hexane layer was washed with acetonitrile concentrated under reduced pressure

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

Procedure: To a solution of (1-allylcyclohexyl)methanol (1.0 g) in N,N-dimethylformamide (7 mL) were added imidazole (661 mg) and triethylchlorosilane (1.41 mL) at room temperature. After stirring the solution at room temperature for 3 hours, N,N-dimethylformamide was added thereto and it was extracted with hexane. The combined hexane layer was washed with acetonitrile and concentrated under reduced pressure to give the title compound (1.70 g). This product was subjected to the subsequent step without further purification. it was extracted with hexane The combined hexane layer was washed with acetonitrile concentrated under reduced pressure