반응 #702135

반응 방정식

Diacetylguanine

acetic anhydride

p-toluenesulfonic acid

dioxolane

→

9-(2-hydroxyethoxymethyl)guanine

수율 21.6%

용매

toluene

반응 조건

후처리

1. 1
   온도to cool for several minutes
2. 2
   온도at reflux for 18 hr
3. 3
   기타The toluene was decanted off
4. 4
   기타the residue triturated several times with benzene
5. 5
   workup.ADDITIONMethanol (10 ml) was added to the residue
6. 6
   기타evaporated under reduced pressure
7. 7
   workup.ADDITIONTo the residue was added 40% aqueous methylamine (10 ml)
8. 8
   온도the mixture heated on a steam bath for 20 min
9. 9
   기타The water and methylamine were removed under reduced pressure, ethanol (10 ml)
10. 10
    workup.ADDITIONwas added
11. 11
    기타evaporated
12. 12
    추출The residue was thoroughly extracted with boiling methanol (700 ml total)
13. 13
    기타the combined extracts evaporated
14. 14
    기타The resulting solid was triturated with cold ethanol
15. 15
    기타recrystallized from methanol

실험 절차

To a mixture of acetic anhydride (1.2 ml) and p-toluenesulfonic acid (0.09 g) was added with stirring dioxolane (1.02 g) - caution, exothermic. The solution was allowed to cool for several minutes. Diacetylguanine (1.45 g) and dry toluene (9 ml) were added and the reaction mixture was stirred at reflux for 18 hr. and then allowed to cool to room temperature. The toluene was decanted off and the residue triturated several times with benzene. Methanol (10 ml) was added to the residue and evaporated under reduced pressure. To the residue was added 40% aqueous methylamine (10 ml) and the mixture heated on a steam bath for 20 min. The water and methylamine were removed under reduced pressure, ethanol (10 ml) was added and evaporated. The residue was thoroughly extracted with boiling methanol (700 ml total) and the combined extracts evaporated. The resulting solid was triturated with cold ethanol and then recrystallized from methanol to give 9-(2-hydroxyethoxymethyl)guanine (0.3 g).

출처