Water → 4,4,5,5,5-Pentafluoropentyl methanesulfonate

HRID 1267733Notes

Reaction equation

HRID 1267733 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[CH2:10][CH2:11][CH2:12][OH:13].[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>ClCCl>[CH3:19][S:20]([O:13][CH2:12][CH2:11][CH2:10][C:9]([F:18])([F:8])[C:14]([F:15])([F:16])[F:17])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5479674,4,5,5,5-Pentafluoropentan-1-ol

Product 1

HCID 120170564,4,5,5,5-Pentafluoropentyl methanesulfonateYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trietylamine (46 ml, 0.330 mol) was added to a solution of 4,4,5,5,5-pentafluoropentan-1-ol (25 g, 0.132 mol) in dichloromethane (50 ml). To this solution, methanesulfonyl chloride (20.4 ml, 0.264 mol) was added at 0° C., followed by stirring for 3 hours at room temperature under argon atmosphere. After the reaction was completed, water was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was washed with 1N aqueous hydrochloric acid, 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 flash column chromatography (eluent: hexane/ethyl acetate=1/1) to give 1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane (34 g, quantitative).

Workup

  1. extractionwas then extracted with dichloromethane
  2. washThe organic layer was washed with 1N aqueous hydrochloric acid, water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-fdf96a7a5c5548a9b0015d12fed429e4
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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