Reaktion #1994268

Reaktionsgleichung

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

Ausbeute 67.0%

Lösungsmittel

water

Eaton's reagent

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigein Synthesis Example 1-3
2. 2
   Sonstigewas separated
3. 3
   WaschenThe water layer was again washed with 30 g of diisopropyl ether
4. 4
   Extraktionafter which extraction
5. 5
   WaschenThe organic layer was washed with water
6. 6
   workup.DISTILLATIONdistilled in vacuum
7. 7
   Sonstigeto remove the solvent
8. 8
   Sonstigepurified by silica gel column chromatography (elute, dichloromethane/methanol)
9. 9
   workup.DISSOLUTIONThe product was dissolved in methyl isobutyl ketone
10. 10
    Waschenwashed with water
11. 11
    workup.DISTILLATIONdistilled in vacuum
12. 12
    Sonstigeto remove the solvent
13. 13
    Sonstigedried in vacuum
14. 14
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
15. 15
    Filtrationfiltered
16. 16
    Sonstigedried
17. 17
    Sonstigeobtaining the target compound

Vorschrift

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%.

Quelle