Reaction #1994266

Reaction equation

triethylammonium 1,1,3,3,3-pentafluoro-2-(4-oxoadamantane-1-carbonyloxy)-1-propanesulfonate

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

tetramethylene sulfoxide

diisopropyl ether

→

4-(2,2,2-trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 1,1,3,3,3-pentafluoro-2-(4-oxoadamantane-1-carbonyloxy)-1-propanesulfonate

Yield 84.0%

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 2008-106045
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
   Otherdried
10. 10
    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 an aqueous solution of triethylammonium 1,1,3,3,3-pentafluoro-2-(4-oxoadamantane-1-carbonyloxy)-1-propanesulfonate (corresponding to 0.0086 mol) synthesized in accordance with the teaching of JP-A 2008-106045, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water, distilled in vacuum to remove the solvent, and dried, obtaining the target compound. Amorphous solids, 5.2 g, yield 84%.

Source