반응 #517962

반응 방정식

NH4Cl

NaH

4-methoxyindole

2-tetrahydropyranyloxy-1-bromoethane

→

desired compound

수율 82.0%

1-(2-hydroxyethyl)-4-methoxyindole

수율 82.0%

용매

DMF

반응 조건

후처리

1. 1
   온도the mixture was gradually heated to room temperature
2. 2
   workup.STIRRINGby stirring the mixture at room temperature for 90 minutes
3. 3
   온도cooled at 0° C.
4. 4
   기타the reaction
5. 5
   추출the resultant was extracted with ethyl acetate (3×10 ml)
6. 6
   세척The obtained organic layers were washed with saturated brine
7. 7
   건조dried over sodium sulfate
8. 8
   기타After removing solids
9. 9
   여과by filtration
10. 10
    기타the solvent was removed under reduced pressure
11. 11
    기타The obtained oil was transferred to a reaction vessel
12. 12
    workup.DISSOLUTIONdissolved in methanol (10 ml)
13. 13
    온도by cooling the obtained solution to 0° C
14. 14
    workup.ADDITIONTo this solution, 1N hydrochloric acid (1 ml) was added
15. 15
    workup.STIRRINGthe solution was stirred at 0° C. for 2 hours
16. 16
    기타After removing the solvent under reduced pressure, water (5 ml)
17. 17
    workup.ADDITIONwas added
18. 18
    추출the resultant was extracted with ethyl acetate (3×20 ml)
19. 19
    세척The obtained organic layers were washed with saturated brine
20. 20
    건조dried over sodium sulfate
21. 21
    기타After removing solids
22. 22
    여과by filtration
23. 23
    기타the solvent was removed under reduced pressure
24. 24
    기타the obtained crude product
25. 25
    기타was purified by silica gel column chromatography

실험 절차

Under argon atmosphere, NaH (283 mg) was added to 4-methoxyindole (516 mg) in DMF (10 ml) and the mixture was stirred at 0° C. for 15 minutes. To this mixture, 2-tetrahydropyranyloxy-1-bromoethane (890 mg) was added and the mixture was gradually heated to room temperature, followed by stirring the mixture at room temperature for 90 minutes. The reaction mixture was added to saturated aqueous NH4Cl solution (5 ml) cooled at 0° C. to stop the reaction, and the resultant was extracted with ethyl acetate (3×10 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure. The obtained oil was transferred to a reaction vessel and dissolved in methanol (10 ml), followed by cooling the obtained solution to 0° C. To this solution, 1N hydrochloric acid (1 ml) was added and the solution was stirred at 0° C. for 2 hours. After removing the solvent under reduced pressure, water (5 ml) was added and the resultant was extracted with ethyl acetate (3×20 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (547 mg, yield: 82%).

출처