반응 #1994268

반응 방정식

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

수율 67.0%

용매

water

Eaton's reagent

water

반응 조건

후처리

1. 1
   기타in Synthesis Example 1-3
2. 2
   기타was separated
3. 3
   세척The water layer was again washed with 30 g of diisopropyl ether
4. 4
   추출after which extraction
5. 5
   세척The organic layer was washed with water
6. 6
   workup.DISTILLATIONdistilled in vacuum
7. 7
   기타to remove the solvent
8. 8
   기타purified by silica gel column chromatography (elute, dichloromethane/methanol)
9. 9
   workup.DISSOLUTIONThe product was dissolved in methyl isobutyl ketone
10. 10
    세척washed with water
11. 11
    workup.DISTILLATIONdistilled in vacuum
12. 12
    기타to remove the solvent
13. 13
    기타dried in vacuum
14. 14
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
15. 15
    여과filtered
16. 16
    기타dried
17. 17
    기타obtaining the target compound

실험 절차

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%.

출처