1-(3,3-Dimethyl-2-oxobutyl)thiolan-1-ium bromide → 2-Oxo-3,3-dimethylbutyl-thiacyclopentanium nonafluorobutanesulfonate

HRID 24969

Reaction equation

HRID 24969 reaction equation
[F:1][C:2]([F:17])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[K+].[Br-].[O:20]=[C:21]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:22][S+:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>O.CO>[F:17][C:2]([F:1])([S:13]([O-:16])(=[O:15])=[O:14])[C:3]([F:11])([F:12])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].[O:20]=[C:21]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:22][S+:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 2

HCID 225645781-(3,3-Dimethyl-2-oxobutyl)thiolan-1-ium bromideHCID 23675274Potassium perfluorobutanesulfonate

Product 1

HCID 225645872-Oxo-3,3-dimethylbutyl-thiacyclopentanium nonafluorobutanesulfonateYield 64.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Potassium perfluorobutanesulfonate (10 g) was dissolved in a mixed solvent comprising 500 ml of water and 100 ml of methanol, and a solution obtained by dissolving 7.7 g of 2-oxo-3,3-dimethylbutyltetrahydrothiophenium bromide in 50 ml of methanol was added to the above solution. The aqueous solution was extracted twice with 100 ml of chloroform, the organic phase was washed with water and concentrated, thereby an oily product was obtained. The above-obtained product was concentrated again with ethyl acetate, thereby a solid product was obtained. The solid product was filtered and re-slurried with diisopropyl ether, to thereby obtain 9 g of 2-oxo-3,3-dimethylbutyltetrahydrothiophenium perfluorobutanesulfonate.

Workup

  1. customa solution obtained
  2. additionwas added to the above solution
  3. extractionThe aqueous solution was extracted twice with 100 ml of chloroform
  4. washthe organic phase was washed with water
  5. concentrationconcentrated
  6. customan oily product was obtained
  7. concentrationThe above-obtained product was concentrated again with ethyl acetate
  8. customa solid product was obtained
  9. filtrationThe solid product was filtered and re-slurried with diisopropyl ether

Sources & evidence

ORD record
ord-71bd1248fad64cd58c8f6ed57ff96111
Source dataset
uspto-grants-2005_02
Patent number
US06858370B2

Linked notes

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