Water → 1-Methanesulfonyloxy-7,7,8,8,8-pentafluorooctane
Reaction equation
[F:1][C:2]([F:14])([C:10]([F:13])([F:12])[F:11])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].O>ClCCl>[CH3:22][S:23]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:14])([F:1])[C:10]([F:11])([F:12])[F:13])(=[O:25])=[O:24]Participants
6
Conditions
- Temperature
- 0 °C
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%).
Workup
- extractionwas then extracted twice with dichloromethane
- washThe combined organic layers were washed with water and saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationAfter distilling off the solvent
- customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/10)
Sources & evidence
- ORD record
- ord-248093b5458b4021929f64b02fc6b5bd
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552068B1
Reaction notes
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