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

HRID 1175258Notes

Reaction equation

HRID 1175258 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-c550af2456a74ca7a98e0a65b713054b
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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