Reacción #517962

Ecuación de reacción

NH4Cl

NaH

4-methoxyindole

2-tetrahydropyranyloxy-1-bromoethane

→

desired compound

Rendimiento 82.0%

1-(2-hydroxyethyl)-4-methoxyindole

Rendimiento 82.0%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was gradually heated to room temperature
2. 2
   workup.STIRRINGby stirring the mixture at room temperature for 90 minutes
3. 3
   Temperaturacooled at 0° C.
4. 4
   Otrothe reaction
5. 5
   Extracciónthe resultant was extracted with ethyl acetate (3×10 ml)
6. 6
   LavadoThe obtained organic layers were washed with saturated brine
7. 7
   Secadodried over sodium sulfate
8. 8
   OtroAfter removing solids
9. 9
   Filtraciónby filtration
10. 10
    Otrothe solvent was removed under reduced pressure
11. 11
    OtroThe obtained oil was transferred to a reaction vessel
12. 12
    workup.DISSOLUTIONdissolved in methanol (10 ml)
13. 13
    Temperaturaby 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
    OtroAfter removing the solvent under reduced pressure, water (5 ml)
17. 17
    workup.ADDITIONwas added
18. 18
    Extracciónthe resultant was extracted with ethyl acetate (3×20 ml)
19. 19
    LavadoThe obtained organic layers were washed with saturated brine
20. 20
    Secadodried over sodium sulfate
21. 21
    OtroAfter removing solids
22. 22
    Filtraciónby filtration
23. 23
    Otrothe solvent was removed under reduced pressure
24. 24
    Otrothe obtained crude product
25. 25
    Otrowas purified by silica gel column chromatography

Procedimiento

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%).

Fuente