Water → 1-Methanesulfonyloxy-5,5,6,6,7,7,8,8,8-nonafluorooctane
Reaction equation
[F:1][C:2]([F:18])([C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][CH2:4][CH2:5][CH2:6][OH:7].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>ClCCl>[CH3:26][S:27]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:18])([F:1])[C:8]([F:16])([F:17])[C:9]([F:14])([F:15])[C:10]([F:11])([F:12])[F:13])(=[O:29])=[O:28]Participants
Procedure
A solution of 5,5,6,6,7,7,8,8,8-nonafluorooctan-1-ol (7.8 g, 26.70 mmol) in dichloromethane (150 ml) was cooled to 0° C. Triethylamine (9.29 ml, 66.75 mmol) and methanesulfonyl chloride (2.48 ml, 32.04 mmol) were added dropwise to the solution, 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=1/4) to give 1-methanesulfonyloxy-5,5,6,6,7,7,8,8,8-nonafluorooctane (8.5 g, Yield 86%).
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=1/4)
Sources & evidence
- ORD record
- ord-e6bc2262b867440bbb367954adf681da
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06552069B1
Reaction notes
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