반응 #155393

반응 방정식

4-(tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate

NH4Cl

→

4-Hydroxyphenyl 10-methylacridan-9-carboxylate

용매

dichloromethane

ethanol

반응 조건

후처리

1. 1
   기타Into a 50 mL round bottom flask equipped with magnetic stirrer
2. 2
   온도reflux condensor
3. 3
   온도heating mantle under an argon atmosphere
4. 4
   온도The reaction mixture was refluxed for 2 hrs
5. 5
   여과filtered
6. 6
   세척The solid was washed with 2×25 mL of ethanol
7. 7
   농축The combined filtrate was concentrated under reduced pressure
8. 8
   기타to give off-white solid
9. 9
   세척washed with 100 mL of deionized water
10. 10
    기타After separation the organic layer
11. 11
    건조was dried over anhydrous Na2SO4
12. 12
    여과filtered
13. 13
    농축The solution was concentrated under reduced pressure
14. 14
    기타purified by column chromatography on silica gel with 10% ethyl acetate-hexane

실험 절차

Into a 50 mL round bottom flask equipped with magnetic stirrer, reflux condensor and heating mantle under an argon atmosphere was charged a solution of 1.42 parts of the 4-(tert-butyldimethylsilyloxy)phenyl 10-methylacridinium-9-carboxylate trifluoromethanesulfonate in 200 mL of ethanol. Then 16 arts NH4Cl was added in five portions, followed by 19.3 parts of Zn in five portions to a hot yellow solutions causing immediate decolorization of the solution. The reaction mixture was refluxed for 2 hrs and filtered. The solid was washed with 2×25 mL of ethanol. The combined filtrate was concentrated under reduced pressure to give off-white solid. The solid was dissolved in 250 mL of dichloromethane and washed with 100 mL of deionized water. After separation the organic layer was dried over anhydrous Na2SO4 and filtered. The solution was concentrated under reduced pressure and purified by column chromatography on silica gel with 10% ethyl acetate-hexane to yield 0.76 parts of 4-Hydroxyphenyl 10-methylacridan-9-carboxylate. The structure was confirmed as:

출처