7,7,8,8,8-pentafluorooctan-1-ol

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 6-(pentafluoroethyl)hexan-1-ol (500 mg) in tetrahydrofuran (10 ml) was added sodium hydride (60% dispersion in mineral oil; 118 mg) and the reaction was stirred at 20° C. for 30 mlnutes. Ethyl bromoacetate (379 mg) was added and the reaction was stirred for a further 3 hours. The reaction was quenched by the addition of ethanol (3 ml) followed by stirring for 30 mlnutes, then 2M sodium hydroxide (3 ml) was added and the reaction was stirred for a further 2 hours. The reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml). The aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid and then extracted with dichloromethane (3×100 ml). The combined organic layers were dried over magnesium sulphate and the solvent was removed in vacuo to give the title compound as a white solid (250 mg). the reaction was stirred for a further 3 hours The reaction was quenched by the addition of ethanol (3 ml) by stirring for 30 mlnutes 2M sodium hydroxide (3 ml) was added the reaction was stirred for a further 2 hours The reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml) The aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid extracted with dichloromethane (3×100 ml) The combined organic layers were dried over magnesium sulphate the solvent was removed in vacuo

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 6-(pentafluoroethyl)hexan-1-ol (500 mg) in tetrahydrofuran (10 ml) was added sodium hydride (60% dispersion in mineral oil; 118 mg) and the reaction was stirred at 20° C. for 30 mlnutes. Ethyl bromoacetate (379 mg) was added and the reaction was stirred for a further 3 hours. The reaction was quenched by the addition of ethanol (3 ml) followed by stirring for 30 mlnutes, then 2M sodium hydroxide (3 ml) was added and the reaction was stirred for a further 2 hours. The reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml). The aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid and then extracted with dichloromethane (3×100 ml). The combined organic layers were dried over magnesium sulphate and the solvent was removed in vacuo to give the title compound as a white solid (250 mg). the reaction was stirred for a further 3 hours The reaction was quenched by the addition of ethanol (3 ml) by stirring for 30 mlnutes 2M sodium hydroxide (3 ml) was added the reaction was stirred for a further 2 hours The reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml) The aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid extracted with dichloromethane (3×100 ml) The combined organic layers were dried over magnesium sulphate the solvent was removed in vacuo

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

Procedure: Into a reaction vessel, 5.00 g (22.7 mmol) of 6-(perfluoroethyl)hexanol (1) and 6.3 ml of pyridine were placed, and 5.21 g (27.3 mmol) of p-toluene-sulfonyl chloride was added little by little thereto under stirring and cooling with ice. After the addition, the system was stirred for 6 hours. The reaction product was poured into iced water, acidified by addition of 6 ml of hydrochloric acid and then extracted with chloroform. The organic layer was washed with salt water and dried with sodium sulfate, followed by solidification by removal of the solvent under a reduced pressure. The residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1, successively, having increasing polarity, thereby obtaining 6.23 g (yield=73.3%) of 6-(perfluoroethyl)hexyl p-toluenesulfonate (2). cooling with ice After the addition the system was stirred for 6 hours extracted with chloroform The organic layer was washed with salt water dried with sodium sulfate followed by solidification by removal of the solvent under a reduced pressure The residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1 successively, having increasing polarity

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

Procedure: Into a reaction vessel, 5.00 g (22.7 mmol) of 6-(perfluoroethyl)hexanol (1) and 6.3 ml of pyridine were placed, and 5.21 g (27.3 mmol) of p-toluene-sulfonyl chloride was added little by little thereto under stirring and cooling with ice. After the addition, the system was stirred for 6 hours. The reaction product was poured into iced water, acidified by addition of 6 ml of hydrochloric acid and then extracted with chloroform. The organic layer was washed with salt water and dried with sodium sulfate, followed by solidification by removal of the solvent under a reduced pressure. The residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1, successively, having increasing polarity, thereby obtaining 6.23 g (yield=73.3%) of 6-(perfluoroethyl)hexyl p-toluenesulfonate (2). cooling with ice After the addition the system was stirred for 6 hours extracted with chloroform The organic layer was washed with salt water dried with sodium sulfate followed by solidification by removal of the solvent under a reduced pressure The residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1 successively, having increasing polarity

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

Procedure: Into a reaction vessel, 5.00 g (22.7 mmol) of 6-(perfluoroethyl)hexanol (1) and 6.3 ml of pyridine were placed, and 5.21 g (27.3 mmol) of p-toluene-sulfonyl chloride was added little by little thereto under stirring and cooling with ice. After the addition, the system was stirred for 6 hours. The reaction product was poured into iced water, acidified by addition of 6 ml of hydrochloric acid and then extracted with chloroform. The organic layer was washed with salt water and dried with sodium sulfate, followed by solidification by removal of the solvent under a reduced pressure. The residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1, successively, having increasing polarity, thereby obtaining 6.23 g (yield=73.3%) of 6-(perfluoroethyl)hexyl p-toluenesulfonate (2). cooling with ice After the addition the system was stirred for 6 hours extracted with chloroform The organic layer was washed with salt water dried with sodium sulfate followed by solidification by removal of the solvent under a reduced pressure The residue was purified by silica gel column chromatography with eluents of hexane/toluene=2/1, toluene, and toluene/ethyl acetate=5/1 successively, having increasing polarity

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

Procedure: 7,7,8,8,8-Pentafluorooctan-1-ol(25 g, 113 mmol) was dissolved in dichloromethane (250 ml), triethylamine(47.4 ml, 339 mmol) and methanesulfonylchloride(17.6 ml, 227 mmol) were added dropwise under cooling to 0° C., and the resulting mixture was stirred for 1 hour. The reaction solution was diluted with water, extracted twice with dichloromethane(200 ml), washed with water and saturated saline solution, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (eluent:ethyl acetate/n-hexane=1/10, v/v) to give 30 g(100 mmol, Yield 89%) of the title compound. extracted twice with dichloromethane(200 ml) washed with water and saturated saline solution dried over anhydrous magnesium sulfate filtered The filtrate was concentrated under reduced pressure the residue was purified by silica gel column chromatography (eluent

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

Procedure: 7,7,8,8,8-Pentafluorooctan-1-ol (25 g, 113 mmol) was dissolved in dichloromethane (250 ml) and cooled to 0° C. To this solution, triethylamine (47.4 ml, 339 mmol) and methanesulfonyl chloride (17.6 ml, 227 mmol) were added dropwise, followed by stirring for 1 hour. After the reaction was completed, water was added to the reaction mixture, which was then extracted twice with dichloromethane. The combined organic layers were washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10) to give 1-methanesulfonyloxy-7,7,8,8,8-pentafluorooctane (30 g, Yield 89%). was then extracted twice with dichloromethane The combined organic layers were washed with water and saturated aqueous sodium chloride dried over anhydrous magnesium sulfate After distilling off the solvent the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10)

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 6-(pentafluoroethyl)hexan-1-ol (500 mg) in tetrahydrofuran (10 ml) was added sodium hydride (60% dispersion in mineral oil; 118 mg) and the reaction was stirred at 20° C. for 30 mlnutes. Ethyl bromoacetate (379 mg) was added and the reaction was stirred for a further 3 hours. The reaction was quenched by the addition of ethanol (3 ml) followed by stirring for 30 mlnutes, then 2M sodium hydroxide (3 ml) was added and the reaction was stirred for a further 2 hours. The reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml). The aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid and then extracted with dichloromethane (3×100 ml). The combined organic layers were dried over magnesium sulphate and the solvent was removed in vacuo to give the title compound as a white solid (250 mg). the reaction was stirred for a further 3 hours The reaction was quenched by the addition of ethanol (3 ml) by stirring for 30 mlnutes 2M sodium hydroxide (3 ml) was added the reaction was stirred for a further 2 hours The reaction mixture was partitioned between dichloromethane (100 ml) and water (100 ml) The aqueous layer was acidified to pH 1 by the addition of 2M hydrochloric acid extracted with dichloromethane (3×100 ml) The combined organic layers were dried over magnesium sulphate the solvent was removed in vacuo