反応 #155393

反応方程式

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

NH4Cl

→

4-Hydroxyphenyl 10-methylacridan-9-carboxylate

溶媒

dichloromethane

ethanol

反応条件

後処理

1. 1
   その他Into a 50 mL round bottom flask equipped with magnetic stirrer
2. 2
   温度reflux condensor
3. 3
   温度heating mantle under an argon atmosphere
4. 4
   温度The reaction mixture was refluxed for 2 hrs
5. 5
   ろ過filtered
6. 6
   洗浄The solid was washed with 2×25 mL of ethanol
7. 7
   濃縮The combined filtrate was concentrated under reduced pressure
8. 8
   その他to give off-white solid
9. 9
   洗浄washed with 100 mL of deionized water
10. 10
    その他After separation the organic layer
11. 11
    乾燥was dried over anhydrous Na2SO4
12. 12
    ろ過filtered
13. 13
    濃縮The solution was concentrated under reduced pressure
14. 14
    その他purified by column chromatography on silica gel with 10% ethyl acetate-hexane

実験手順

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:

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