Water → Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

HRID 878617Notes

Reaction equation

HRID 878617 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCN(CC)CC.[F:19][C:20]([F:24])([F:23])[CH2:21][OH:22].O>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:22][CH2:21][C:20]([F:24])([F:23])[F:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 64092,2,2-TrifluoroethanolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)Yield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methylbenzenesulfonyl chloride (3.4 g, 17.83 mmol) and Et3N (3.61 g, 35.66 mmol) in DCM (80 mL) was added 2,2,2-trifluoroethan-1-ol (2.32 g, 23.18 mmol) slowly, the mixture was then stirred at r.t. until TLC showed no starting material. Water was added to the reaction mixture, and extracted with DCM, collected the organic phase and washed with brine, dried with anhydrous Na2SO4, removed the solvent to give 4.2 g of the title compound (93%). 1H NMR (400 MHz, CDCl3): δ 2.47 (3H, s), 4.34 (2H, q, J=8.0 Hz), 7.38 (2H, d, J=8.0 Hz), 7.81 (2H, d, J=8.0 Hz).

Workup

  1. extractionextracted with DCM
  2. customcollected the organic phase
  3. washwashed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. customremoved the solvent

Sources & evidence

ORD record
ord-1021011a24a941448fa53a7f1a99ee35
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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