2,2,2-Trifluoroethanol → 3-(2,2,2-Trifluoroethoxy)phenoxathiin 10,10-dioxide

HRID 1872878Notes

Reaction equation

HRID 1872878 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[K+].F[C:10]1[CH:11]=[CH:12][C:13]2[S:14](=[O:25])(=[O:24])[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3>CN(C)C=O>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][C:10]1[CH:11]=[CH:12][C:13]2[S:14](=[O:24])(=[O:25])[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 82127Potassium hydrideHCID 186877423-Fluorophenoxathiin 10,10-dioxide

Product 1

HCID 98623143-(2,2,2-Trifluoroethoxy)phenoxathiin 10,10-dioxideYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1,1-Trifluoro-2-ethanol (Aldrich) (0.44 g, 0.004 mole) was added to a stirred, ice-bath cooled mixture of potassium hydride (approximate 50% dispersion in mineral oil) (Aldrich) (0.32 g, 0.004 mole) and N,N-dimethylformamide (75 mL). The ice-bath was removed, and the reaction was stirred at ambient temperature for 1 hour. 3-Fluorophenoxathiin 10,10-dioxide (Example 47) (1.00 g, 0.004 mole) was added, and the mixture was heated at reflux under nitrogen for 2 hours. The reaction was cooled, and the volatiles were removed by spin evaporation in vacuo. The residue was purified by column chromatography on Silica Gel 60 using ethyl acetate-hexanes:2-8. The appropriate column fractions were combined, and the volatiles were removed by spin evaporation in vacuo to give 0.43 g (32% yield) of 3-(2,2,2-trifluoroethoxy)phenoxathiin 10,10-dioxide. Recrystallization from ethanol gave 0.23 g (17% yield) of 3-(2,2,2-trifluoroethoxy)phenoxathiin 10,10-dioxide, m.p. 165-166° C.

Workup

  1. temperaturecooled
  2. customThe ice-bath was removed
  3. temperaturethe mixture was heated
  4. temperatureat reflux under nitrogen for 2 hours
  5. temperatureThe reaction was cooled
  6. customthe volatiles were removed by spin evaporation in vacuo
  7. customThe residue was purified by column chromatography on Silica Gel 60 using ethyl acetate-hexanes
  8. customthe volatiles were removed by spin evaporation in vacuo

Sources & evidence

ORD record
ord-9a870610db104a6fa66dc7f6c7a46036
Source dataset
uspto-grants-2000_08
Patent number
US06110961

Reaction notes

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