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

HRID 1461408Notes

Reaction equation

HRID 1461408 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 and then a mixture of 1.5 parts of N,N-dimethyl-4-pyridinamine and 25 parts of ethyl acetate. After stirring overnight at room temperature, the reaction mixture was filtered and the filtrate was evaporated. The residue was stirred in water. The solid was filtered off and dissolved in dichloromethane. This solution was dried, filtered and evaporated. The residue was successively triturated with petroleumether and 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. (interm. 12).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. stirringThe residue was stirred in water
  4. filtrationThe solid was filtered off
  5. dissolutiondissolved in dichloromethane
  6. customThis solution was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was successively triturated with petroleumether
  10. customcrystallized from 2-propanol
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-576e584f515343c5b78e1cfd1d9a5834
Source dataset
uspto-grants-1991_12
Patent number
US05075309

Reaction notes

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