2,2,2-Trifluoroethanol → 2,2,2-Trifluoroethyl 2-naphthalenesulfonate

HRID 2106774Notes

Reaction equation

HRID 2106774 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].C(N(CC)CC)C.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24](Cl)(=[O:26])=[O:25]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[S:24]([O:4][CH2:3][C:2]([F:6])([F:5])[F:1])(=[O:25])=[O:26]

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 71252-Naphthalenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 150356142,2,2-Trifluoroethyl 2-naphthalenesulfonateYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 25.0 parts of 2,2,2-trifluoroethanol in 175 parts of N,N-diethylethanamine were added portionwise 62.2 parts of 2-naphthalenesulfonyl chloride. Upon completion, a mixture of 1.5 parts of N,N-dimethyl-4-pyridinamine and 25 parts of ethyl acetate was added during a period of 20 minutes. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was stirred in water and solidified product was filtered off under reduced pressure. The precipitated product was dissolved in dichloromethane. The organic layer was dried, filtered and evaporated in vacuo. The residue was treated with petroleum ether. After filtration, the precipitated product was crystallized from 2-propanol. The product was filtered off and dried, yielding 65.3 parts (89%) of 2,2,2-trifluoroethyl 2-naphthalenesulfonate; mp. 72.7° C. (int. 36).

Workup

  1. additionwas added during a period of 20 minutes
  2. additionUpon complete addition
  3. filtrationThe reaction mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. stirringThe residue was stirred in water
  6. filtrationsolidified product was filtered off under reduced pressure
  7. dissolutionThe precipitated product was dissolved in dichloromethane
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. additionThe residue was treated with petroleum ether
  12. filtrationAfter filtration
  13. customthe precipitated product was crystallized from 2-propanol
  14. filtrationThe product was filtered off
  15. customdried

Sources & evidence

ORD record
ord-796524b119e248cb9e7ccb7fd79a3e87
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

Loading…