Réaction #1994268

Équation de réaction

benzyltrimethylammonium 1,1,3,3,3-pentafluoro-2-(3,7,12-trioxocholanoyloxy)-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-(3,7,12-trioxocholanoyloxy)-1-propanesulfonate

Rendement 67.0%

Solvants

water

Eaton's reagent

water

Conditions de réaction

Traitement

1. 1
   Autrein Synthesis Example 1-3
2. 2
   Autrewas separated
3. 3
   LavageThe water layer was again washed with 30 g of diisopropyl ether
4. 4
   Extractionafter which extraction
5. 5
   LavageThe organic layer was washed with water
6. 6
   workup.DISTILLATIONdistilled in vacuum
7. 7
   Autreto remove the solvent
8. 8
   Autrepurified by silica gel column chromatography (elute, dichloromethane/methanol)
9. 9
   workup.DISSOLUTIONThe product was dissolved in methyl isobutyl ketone
10. 10
    Lavagewashed with water
11. 11
    workup.DISTILLATIONdistilled in vacuum
12. 12
    Autreto remove the solvent
13. 13
    Autredried in vacuum
14. 14
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
15. 15
    Filtrationfiltered
16. 16
    Autredried
17. 17
    Autreobtaining the target compound

Mode opératoire

In 6 g of Eaton's reagent (Aldrich, diphosphorus pentoxide/methanesulfonic acid solution) was dispersed 3.4 g (0.0150 mol) of 1-(2,2,2-trifluoroethoxy)naphthalene in Synthesis Example 1-3. With stirring, 3.2 g (0.0300 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 (0.0100 mol) of benzyltrimethylammonium 1,1,3,3,3-pentafluoro-2-(3,7,12-trioxocholanoyloxy)-1-propanesulfonate in Synthesis Example 1-7, 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 purified by silica gel column chromatography (elute, dichloromethane/methanol). The product was dissolved in methyl isobutyl ketone, washed with water, distilled in vacuum to remove the solvent, and dried in vacuum. The product was poured into isopropyl ether for crystallization, filtered and dried, obtaining the target compound. White crystals, 6.2 g, yield 67%.

Source