반응 #1994265

반응 방정식

benzyltrimethylammonium 2-(adamantane-1-carbonyloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

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

tetramethylene sulfoxide

diisopropyl ether

→

4-(2,2,2-trifluoroethoxy)-1-naphthyl-tetrahydrothiophenium 2-(adamantane-1-carbonyloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate

수율 78.0%

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.DISTILLATIONthe solvent was distilled off in vacuum
7. 7
   기타The residue was purified by silica gel column chromatography (elute, dichloromethane/methanol)
8. 8
   workup.DISSOLUTIONIt was dissolved in methyl isobutyl ketone
9. 9
   세척washed with water
10. 10
    기타followed by solvent removal and vacuum
11. 11
    기타drying
12. 12
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
13. 13
    여과filtered
14. 14
    기타dried
15. 15
    기타obtaining the target compound

실험 절차

In 6 g of Eaton's reagent (Aldrich, diphosphorus pentoxide/methanesulfonic acid solution) was dispersed 3 g (0.0127 mol) of 1-(2,2,2-trifluoroethoxy)naphthalene in Synthesis Example 1-3. With stirring, 2.6 g (0.0253 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 5.5 g (0.0101 mol) of benzyltrimethylammonium 2-(adamantane-1-carbonyloxy)-1,1,3,3,3-pentafluoropropane-1-sulfonate in Synthesis Example 1-2, after which extraction was effected twice with 50 g of dichloromethane. The organic layer was washed with water, and the solvent was distilled off in vacuum. The residue was purified by silica gel column chromatography (elute, dichloromethane/methanol). It was dissolved in methyl isobutyl ketone and washed with water, followed by solvent removal and vacuum drying. The product was poured into isopropyl ether for crystallization, filtered and dried, obtaining the target compound. White crystal, 5.6 g, yield 78%.

출처