反応 #1994268

反応方程式

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

収率 67.0%

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.DISTILLATIONdistilled in vacuum
7. 7
   その他to remove the solvent
8. 8
   その他purified by silica gel column chromatography (elute, dichloromethane/methanol)
9. 9
   workup.DISSOLUTIONThe product was dissolved in methyl isobutyl ketone
10. 10
    洗浄washed with water
11. 11
    workup.DISTILLATIONdistilled in vacuum
12. 12
    その他to remove the solvent
13. 13
    その他dried in vacuum
14. 14
    workup.ADDITIONThe product was poured into isopropyl ether for crystallization
15. 15
    ろ過filtered
16. 16
    その他dried
17. 17
    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 3.4 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%.

出典