Pyridine → 2,2,2-Trifluoroethyl trifluoromethanesulfonate

HRID 1408772Notes

Reaction equation

HRID 1408772 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].N1C=CC=CC=1.C(Cl)Cl.[O:16](S(C(F)(F)F)(=O)=O)[S:17]([C:20]([F:23])([F:22])[F:21])(=O)=[O:18]>O>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:18])=[O:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 64092,2,2-TrifluoroethanolHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 2,2,2-trifluoro-ethanol (6.2 mL), pyridine (6.8 mL) and CH2Cl2 (20 mL) cooled in an ice bath. Add Tf2O (25 g) over about 45 minutes. After 15 minutes, add water, separate the layers and extract with water. The organic layer was dried over Na2SO4 and concentrated through a short path distillation apparatus (8 g, 54%).

Workup

  1. customseparate the layers
  2. extractionextract with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated through a short path distillation apparatus (8 g, 54%)

Sources & evidence

ORD record
ord-86a1565051a340ccb3735e038f322d85
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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