Reacción #1994267

Ecuación de reacción

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

Rendimiento 87.0%

Disolventes

water

Eaton's reagent

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroin Synthesis Example 1-3
2. 2
   Otrowas separated
3. 3
   LavadoThe water layer was again washed with 30 g of diisopropyl ether
4. 4
   Otrosynthesized in accordance with the teaching of JP-A 2007-145797
5. 5
   Extracciónafter which extraction
6. 6
   LavadoThe organic layer was washed with water
7. 7
   workup.DISTILLATIONdistilled in vacuum
8. 8
   Otroto remove the solvent
9. 9
   workup.ADDITIONThe residue was poured into isopropyl ether for crystallization
10. 10
    Filtraciónfiltered
11. 11
    Otrodried
12. 12
    Otroobtaining the target compound

Procedimiento

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%.

Fuente