Water → 1-Methanesulfonyloxy-4,4,5,5,6,6,7,7,7-nonafluoroheptane

HRID 1267467Notes

Reaction equation

HRID 1267467 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:22])([C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])[CH2:8][CH2:9][CH2:10][OH:11].C(N(CC)CC)C.O>ClCCl>[CH3:1][S:2]([O:11][CH2:10][CH2:9][CH2:8][C:7]([F:22])([F:6])[C:12]([F:20])([F:21])[C:13]([F:18])([F:19])[C:14]([F:15])([F:16])[F:17])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27790914,4,5,5,6,6,7,7,7-Nonafluoro-1-heptanol

Product 1

HCID 120167731-Methanesulfonyloxy-4,4,5,5,6,6,7,7,7-nonafluoroheptaneYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. extractionwas then extracted with dichloromethane
  2. washThe organic layer was 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=1/3)

Sources & evidence

ORD record
ord-972a09ee2dd64302abb7e85042eaaa7b
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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