Reaktion #1994265

Reaktionsgleichung

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

Ausbeute 78.0%

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.DISTILLATIONthe solvent was distilled off in vacuum
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (elute, dichloromethane/methanol)
8. 8
   workup.DISSOLUTIONIt was dissolved in methyl isobutyl ketone
9. 9
   Waschenwashed with water
10. 10
    Sonstigefollowed by solvent removal and vacuum
11. 11
    Sonstigedrying
12. 12
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
13. 13
    Filtrationfiltered
14. 14
    Sonstigedried
15. 15
    Sonstigeobtaining the target compound

Vorschrift

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%.

Quelle