5-cyclohexylpentan-1-ol

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

Procedure: To a portion of 100 mL glacial acetic acid, purged with argon, was added 5.62 g of PtO2 (Aldrich) followed by a solution of 25.00 g (152.2 mmol, Aldrich) of 5-phenyl-1-pentanol in 100 mL glacial acetic acid. The reaction vessel was evacuated and purged with H2 three times, the the reaction mixture was stirred under H2 (1 atm) of 22 hours. The reaction was not complete by thin layer chromatography. A second portion of 3.25 (Aldrich) of PtO2 was added and the reaction was stirred under H2 (1 atm) for an additional 32 hours. The mixture was filtered through a 0.4 μM polycarbonate filter, the filtrate was concentrated in vacuo and then azeotroped four times with toluene to give 28.08 g (164.9 mmol, 100%) of a cloudy liquid. 1H NMR indicated the crude material was about a 2:1 mixture of the alcohol title compound and the corresponding acetate. To a portion of 100 mL glacial acetic acid, purged with argon was added 5.62 g of PtO2 (Aldrich) The reaction vessel was evacuated purged with H2 three times A second portion of 3.25 (Aldrich) of PtO2 was added the reaction was stirred under H2 (1 atm) for an additional 32 hours The mixture was filtered through a 0.4 μM polycarbonate filter the filtrate was concentrated in vacuo azeotroped four times with toluene to give 28.08 g (164.9 mmol, 100%) of a cloudy liquid

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

Procedure: To a stirred solution of 5-cyclohexylpentanol (1.74 g., 10.25 mmol) and pyridine (0.94 g., 11.1 mmol) at 0° under argon was added phosphorus tribromide (1.21 g., 4.5 mmol) dropwise. The reaction mixture became viscous, therefore 25 ml tetrahydrofuran was added. This mixture was stirred for 1.5 hours at room temperature, then partitioned between ethyl ether and 5% aqueous hydrochloric acid. The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil. Purification by flash chromatography (silica, hexane) yielded the desired alkyl halide. partitioned between ethyl ether and 5% aqueous hydrochloric acid The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution dried over magnesium sulfate filtered concentrated to give a dark yellow oil Purification by flash chromatography (silica, hexane)

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

Procedure: To a stirred solution of 5-cyclohexylpentanol (1.74 g., 10.25 mmol) and pyridine (0.94 g., 11.1 mmol) at 0° under argon was added phosphorus tribromide (1.21 g., 4.5 mmol) dropwise. The reaction mixture became viscous, therefore 25 ml tetrahydrofuran was added. This mixture was stirred for 1.5 hours at room temperature, then partitioned between ethyl ether and 5% aqueous hydrochloric acid. The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil. Purification by flash chromatography (silica, hexane) yielded the desired alkyl halide. partitioned between ethyl ether and 5% aqueous hydrochloric acid The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution dried over magnesium sulfate filtered concentrated to give a dark yellow oil Purification by flash chromatography (silica, hexane)

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

Procedure: To a solution of 5-phenylpentanol (2.21 g., 13.5 mmol) in ten ml glacial acetic acid was added amorphous platinum oxide (0.40 g., 1.76 mmol, oxygen activated). This mixture was subjected to three atm. of hydrogen with agitation (Parr hydrogenator) at room temperature for four hours. The reaction mixture was diluted with ethyl ether, filtered through celite, washed repeatedly with saturated sodium bicarbonate, followed by water and saturated sodium chloride solution. The organic portion was filtered, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol. filtered through celite washed repeatedly with saturated sodium bicarbonate The organic portion was filtered dried over magnesium sulfate filtered concentrated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under nitrogen atmosphere, at 0° C., to a stirring mixture of 2M LiAlH4 (13.04 mL, 26.08 mmol) solution in Et2O in dry Et2O (67 mL), 5-cyclohexylpentanoic acid (1.2 g, 6.52 mmol) in dry Et2O (2 mL) was added dropwise. The mixture was left to react at rt for 4 h, then upon full conversion of the starting material, at 0° C., H2O (13.04 mL), 3M KOH (13.04 mL) solution and H2O (43.65 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the remaining organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.98 g, 88%) as a colorless oil. 1H NMR (DMSO-d6): δ 0.77-0.93 (m, 2H), 1.06-1.34 (m, 10H), 1.35-1.47 (m, 2H), 1.56-1.76 (m, 5H), 3.37 (t, J=6.6 Hz, 2H). The mixture was left to react at rt for 4 h filtered to remove the solid residue the remaining organic phase dried over Na2SO4 The organic solution was again filtered concentrated to dryness

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under nitrogen atmosphere, at 0° C., to a stirring mixture of 2M LiAlH4 (13.04 mL, 26.08 mmol) solution in Et2O in dry Et2O (67 mL), 5-cyclohexylpentanoic acid (1.2 g, 6.52 mmol) in dry Et2O (2 mL) was added dropwise. The mixture was left to react at rt for 4 h, then upon full conversion of the starting material, at 0° C., H2O (13.04 mL), 3M KOH (13.04 mL) solution and H2O (43.65 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the remaining organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.98 g, 88%) as a colorless oil. 1H NMR (DMSO-d6): δ 0.77-0.93 (m, 2H), 1.06-1.34 (m, 10H), 1.35-1.47 (m, 2H), 1.56-1.76 (m, 5H), 3.37 (t, J=6.6 Hz, 2H). The mixture was left to react at rt for 4 h filtered to remove the solid residue the remaining organic phase dried over Na2SO4 The organic solution was again filtered concentrated to dryness

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

Procedure: To a portion of 100 mL glacial acetic acid, purged with argon, was added 5.62 g of PtO2 (Aldrich) followed by a solution of 25.00 g (152.2 mmol, Aldrich) of 5-phenyl-1-pentanol in 100 mL glacial acetic acid. The reaction vessel was evacuated and purged with H2 three times, the the reaction mixture was stirred under H2 (1 atm) of 22 hours. The reaction was not complete by thin layer chromatography. A second portion of 3.25 (Aldrich) of PtO2 was added and the reaction was stirred under H2 (1 atm) for an additional 32 hours. The mixture was filtered through a 0.4 μM polycarbonate filter, the filtrate was concentrated in vacuo and then azeotroped four times with toluene to give 28.08 g (164.9 mmol, 100%) of a cloudy liquid. 1H NMR indicated the crude material was about a 2:1 mixture of the alcohol title compound and the corresponding acetate. To a portion of 100 mL glacial acetic acid, purged with argon was added 5.62 g of PtO2 (Aldrich) The reaction vessel was evacuated purged with H2 three times A second portion of 3.25 (Aldrich) of PtO2 was added the reaction was stirred under H2 (1 atm) for an additional 32 hours The mixture was filtered through a 0.4 μM polycarbonate filter the filtrate was concentrated in vacuo azeotroped four times with toluene to give 28.08 g (164.9 mmol, 100%) of a cloudy liquid

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

Procedure: To a stirred solution of 5-cyclohexylpentanol (1.74 g., 10.25 mmol) and pyridine (0.94 g., 11.1 mmol) at 0° under argon was added phosphorus tribromide (1.21 g., 4.5 mmol) dropwise. The reaction mixture became viscous, therefore 25 ml tetrahydrofuran was added. This mixture was stirred for 1.5 hours at room temperature, then partitioned between ethyl ether and 5% aqueous hydrochloric acid. The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil. Purification by flash chromatography (silica, hexane) yielded the desired alkyl halide. partitioned between ethyl ether and 5% aqueous hydrochloric acid The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution dried over magnesium sulfate filtered concentrated to give a dark yellow oil Purification by flash chromatography (silica, hexane)

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

Procedure: To a solution of 5-phenylpentanol (2.21 g., 13.5 mmol) in ten ml glacial acetic acid was added amorphous platinum oxide (0.40 g., 1.76 mmol, oxygen activated). This mixture was subjected to three atm. of hydrogen with agitation (Parr hydrogenator) at room temperature for four hours. The reaction mixture was diluted with ethyl ether, filtered through celite, washed repeatedly with saturated sodium bicarbonate, followed by water and saturated sodium chloride solution. The organic portion was filtered, dried over magnesium sulfate, filtered and concentrated to give the desired alcohol. filtered through celite washed repeatedly with saturated sodium bicarbonate The organic portion was filtered dried over magnesium sulfate filtered concentrated