Water → 2-(2,2,2-Trifluoroethoxy)ethyl p-toluenesulfonate

HRID 425069Notes

Reaction equation

HRID 425069 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][O:4][CH2:5][CH2:6][OH:7].[S:10](Cl)([C:13]1[CH:19]=[CH:18][C:16]([CH3:17])=[CH:15][CH:14]=1)(=[O:12])=[O:11].O>N1C=CC=CC=1>[CH3:17][C:16]1[CH:18]=[CH:19][C:13]([S:10]([O:7][CH2:6][CH2:5][O:4][CH2:3][C:2]([F:9])([F:8])[F:1])(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 2558542-(2,2,2-Trifluoroethoxy)ethan-1-ol

Product 1

HCID 220332952-(2,2,2-Trifluoroethoxy)ethyl p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(2,2,2-trifluoroethoxy)ethanol (intermediate BR) (12.7 g) was dissolved in anhydrous pyridine, then TsCl (1.3 eq) was added, and the mixture was stirred at room temperature for 16 h, after which TLC showed the reaction was complete. Then the mixture was poured into water, extracted with EA, washed with water and brine, and dried with anhydrous Na2SO4. The solvent was removed and the residue purified by column chromatography to obtain intermediate BS (0.3 g).

Workup

  1. extractionextracted with EA
  2. washwashed with water and brine
  3. dry with materialdried with anhydrous Na2SO4
  4. customThe solvent was removed
  5. customthe residue purified by column chromatography
  6. customto obtain intermediate BS (0.3 g)

Sources & evidence

ORD record
ord-12b4bf431e7242bf8047ae71357f25ca
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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