Water → 1-Methanesulfonyloxy-6,6,7,7,7-pentafluoroheptane

HRID 1267741Notes

Reaction equation

HRID 1267741 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[F:13][C:14]([F:25])([C:21]([F:24])([F:23])[F:22])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20].O>ClCCl>[CH3:8][S:9]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]([F:25])([F:13])[C:21]([F:22])([F:23])[F:24])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 120170636,6,7,7,7-Pentafluoroheptan-1-ol

Product 1

HCID 120170641-Methanesulfonyloxy-6,6,7,7,7-pentafluoroheptaneYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (25.83 ml, 185.3 mmol) and methanesulfonyl chloride (6.9 ml, 88.9 mmol) were added dropwise to a solution of 6,6,7,7,7-pentafluoroheptan-1-ol (14.1 g, 74.1 mmol) in dichloromethane (350 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 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-6,6,7,7,7-pentafluoroheptane (17.3 g, Yield 82%).

Workup

  1. extractionwas then extracted twice with dichloromethane
  2. washThe combined organic layers were washed with 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 column chromatography (eluent: ethyl acetate/hexane=1/10)

Sources & evidence

ORD record
ord-cdd26ddf1c6246c7864ac58b959853a6
Source dataset
uspto-grants-2003_04
Patent number
US06552068B1

Reaction notes

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