4-Toluenesulfonyl chloride → 2-(2,2,2-Trifluoroethoxy)ethyl p-toluenesulfonate

HRID 658259Notes

Reaction equation

HRID 658259 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][O:4][CH2:5][CH2:6][OH:7].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:7][CH2:6][CH2:5][O:4][CH2:3][C:2]([F:9])([F:8])[F:1])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 2558542-(2,2,2-Trifluoroethoxy)ethan-1-ol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,2,2-trifluoroethoxy)ethanol (1 eq.) in DCM (0.2 M) was added p-toluenesulfonyl chloride (1.3 eq.) and triethylamine (1.5 eq.). The reaction was stirred at rt for 18 h. The reaction was quenched with saturated NH4Cl aqueous solution and extracted with DCM. The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 30% ether in hexane) to afford the title compound as an oil.

Workup

  1. customThe reaction was quenched with saturated NH4Cl aqueous solution
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash column chromatography (SiO2, 30% ether in hexane)

Sources & evidence

ORD record
ord-4b06a8c6e19b40db9fb6084cc28ddb2e
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Reaction notes

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