反応 #1994265

反応方程式

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

収率 78.0%

溶媒

water

Eaton's reagent

water

反応条件

後処理

1. 1
   その他in Synthesis Example 1-3
2. 2
   その他was separated
3. 3
   洗浄The water layer was again washed with 30 g of diisopropyl ether
4. 4
   抽出after which extraction
5. 5
   洗浄The organic layer was washed with water
6. 6
   workup.DISTILLATIONthe solvent was distilled off in vacuum
7. 7
   その他The residue was purified by silica gel column chromatography (elute, dichloromethane/methanol)
8. 8
   workup.DISSOLUTIONIt was dissolved in methyl isobutyl ketone
9. 9
   洗浄washed with water
10. 10
    その他followed by solvent removal and vacuum
11. 11
    その他drying
12. 12
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
13. 13
    ろ過filtered
14. 14
    その他dried
15. 15
    その他obtaining the target compound

実験手順

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%.

出典