Reaction #1994267

Reaction equation

sodium 2-benzoyloxy-1,1,3,3,3-pentafluoropropanesulfonate

1-(2,2,2-trifluoroethoxy)naphthalene

tetramethylene sulfoxide

diisopropyl ether

→

4-(2,2,2-trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 2-benzoyloxy-1,1,3,3,3-pentafluoro-propane-1-sulfonate

Yield 87.0%

Solvents

water

Eaton's reagent

water

Conditions

Workup

1. 1
   Otherin Synthesis Example 1-3
2. 2
   Otherwas separated
3. 3
   WashThe water layer was again washed with 30 g of diisopropyl ether
4. 4
   Othersynthesized in accordance with the teaching of JP-A 2007-145797
5. 5
   Extractionafter which extraction
6. 6
   WashThe organic layer was washed with water
7. 7
   workup.DISTILLATIONdistilled in vacuum
8. 8
   Otherto remove the solvent
9. 9
   workup.ADDITIONThe residue was poured into isopropyl ether for crystallization
10. 10
    Filtrationfiltered
11. 11
    Otherdried
12. 12
    Otherobtaining the target compound

Procedure

In 6 g of Eaton's reagent (Aldrich, diphosphorus pentoxide/methanesulfonic acid solution) was dispersed 2.4 g (0.0107 mol) of 1-(2,2,2-trifluoroethoxy)naphthalene in Synthesis Example 1-3. With stirring, 2.2 g (0.0214 mol) of tetramethylene sulfoxide was added dropwise to the dispersion. The solution was matured overnight at room temperature and combined with 30 g of water and 30 g of diisopropyl ether, from which a water layer was separated. The water layer was again washed with 30 g of diisopropyl ether. This aqueous solution was combined with 3.4 g (0.0095 mol) of sodium 2-benzoyloxy-1,1,3,3,3-pentafluoropropanesulfonate synthesized in accordance with the teaching of JP-A 2007-145797, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water and distilled in vacuum to remove the solvent. The residue was poured into isopropyl ether for crystallization, filtered and dried, obtaining the target compound. White crystals, 5.3 g, yield 87%.

Source