Water → 2-(2,2,2-Trifluoroethoxy)ethyl thioacetate

HRID 1792374Notes

Reaction equation

HRID 1792374 reaction equation
C1(C)C=CC(S([O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])(=O)=O)=CC=1.[C:20]([O-])(=[S:22])[CH3:21].[K+].O>CC(C)=O>[C:20]([O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]([F:16])([F:17])[F:18])(=[S:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 220332952-(2,2,2-Trifluoroethoxy)ethyl p-toluenesulfonateHCID 23670855Potassium ethanethioate

Product 1

HCID 537851902-(2,2,2-Trifluoroethoxy)ethyl thioacetateYield 87.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(2,2,2-trifluoroethoxy)ethyl p-toluenesulfonate (14.0 g, 47 mmol) and potassium thioacetate (10.0 g, 88 mmol) were dissolved in acetone (100 ml) and the mixture was stirred at room temperature for 2 days. The mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. After concentration, silica gel column chromatography (n-hexane/ethyl acetate=10/1) gave 2-(2,2,2-Trifluoroethoxy)ethyl thioacetate (8.3 g, 87%)

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationAfter concentration, silica gel column chromatography (n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-9e49ffc9799b405ba0b3b5399a789cc0
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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