تفاعل #517962

معادلة التفاعل

NH4Cl

NaH

4-methoxyindole

2-tetrahydropyranyloxy-1-bromoethane

→

desired compound

المردود 82.0%

1-(2-hydroxyethyl)-4-methoxyindole

المردود 82.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was gradually heated to room temperature
2. 2
   workup.STIRRINGby stirring the mixture at room temperature for 90 minutes
3. 3
   درجة الحرارةcooled at 0° C.
4. 4
   أخرىthe reaction
5. 5
   استخلاصthe resultant was extracted with ethyl acetate (3×10 ml)
6. 6
   غسيلThe obtained organic layers were washed with saturated brine
7. 7
   تجفيفdried over sodium sulfate
8. 8
   أخرىAfter removing solids
9. 9
   ترشيحby filtration
10. 10
    أخرىthe solvent was removed under reduced pressure
11. 11
    أخرىThe obtained oil was transferred to a reaction vessel
12. 12
    workup.DISSOLUTIONdissolved in methanol (10 ml)
13. 13
    درجة الحرارةby 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
    أخرىAfter removing the solvent under reduced pressure, water (5 ml)
17. 17
    workup.ADDITIONwas added
18. 18
    استخلاصthe resultant was extracted with ethyl acetate (3×20 ml)
19. 19
    غسيلThe obtained organic layers were washed with saturated brine
20. 20
    تجفيفdried over sodium sulfate
21. 21
    أخرىAfter removing solids
22. 22
    ترشيحby filtration
23. 23
    أخرىthe solvent was removed under reduced pressure
24. 24
    أخرىthe obtained crude product
25. 25
    أخرىwas purified by silica gel column chromatography

الإجراء التجريبي

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%).

المصدر