4,4,5,5,6,6,7,7,7-nonafluoroheptan-1-ol

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

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

Procedure: Methanesulfonyl chloride (2.8 ml, 36.72 mmol) was added to a solution of 4,4,5,5,6,6,7,7,7-nonafluoroheptan-1-ol (6.0 g, 21.6 mmol) and triethylamine (6.0 ml, 43.2 mmol) in dichloromethane (60 ml) at 0° C., followed by stirring for 1 hour. After the reaction was completed, water was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was 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=1/3) to give 1-methanesulfonyloxy-4,4,5,5,6,6,7,7,7-nonafluoroheptane (6.73 g, Yield 92.2%) as a colorless oil. was then extracted with dichloromethane The organic layer was 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=1/3)

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

Procedure: Borane-methyl sulfide complex (5.2 ml, 52.2 mmol) was slowly added to a solution of 4,4,5,5,6,6,7,7,7-nonafluoroheptanoic acid (5.10 g, 17.4 mmol) in anhydrous tetrahydrofuran (50 ml) at −50° C. The reaction mixture was stirred for 4 hours at room temperature and cooled to 0° C., followed by addition of methanol. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5→1/3) to give 4,4,5,5,6,6,7,7,7-nonafluoroheptan-1-ol (4.7 g, Yield 97%) as a colorless oil. cooled to 0° C. After distilling off the solvent the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5→1/3)