تفاعل #1994265

معادلة التفاعل

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

المردود 78.0%

المذيبات

water

Eaton's reagent

water

ظروف التفاعل

المعالجة

1. 1
   أخرىin Synthesis Example 1-3
2. 2
   أخرىwas separated
3. 3
   غسيلThe water layer was again washed with 30 g of diisopropyl ether
4. 4
   استخلاصafter which extraction
5. 5
   غسيلThe organic layer was washed with water
6. 6
   workup.DISTILLATIONthe solvent was distilled off in vacuum
7. 7
   أخرىThe residue was purified by silica gel column chromatography (elute, dichloromethane/methanol)
8. 8
   workup.DISSOLUTIONIt was dissolved in methyl isobutyl ketone
9. 9
   غسيلwashed with water
10. 10
    أخرىfollowed by solvent removal and vacuum
11. 11
    أخرىdrying
12. 12
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
13. 13
    ترشيحfiltered
14. 14
    أخرىdried
15. 15
    أخرىobtaining the target compound

الإجراء التجريبي

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%.

المصدر