반응 #439272

반응 방정식

DMF

phosphorus oxychloride

sodium hydroxide

3-(4-fluorophenyl)-1-isopropyl-1H-indole

DMF

DMF

→

brown oil

3-(4-Fluorophenyl)-1-isopropyl-1H-indole-2-carbaldehyde

용매

water

반응 조건

후처리

1. 1
   기타equipped with a magnetic stirrer
2. 2
   온도reflux condenser
3. 3
   온도nitrogen delivery line, and cooled
4. 4
   기타does not exceed 10° C
5. 5
   온도The reaction mixture is then heated to 80° C.
6. 6
   workup.ADDITIONare added dropwise in the course of 30 min
7. 7
   workup.STIRRINGStirring
8. 8
   온도Cooling
9. 9
   기타The reaction mixture is transferred into a dropping funnel
10. 10
    workup.STIRRINGwith stirring
11. 11
    추출The aqueous phase is extracted four times with 50 ml of toluene
12. 12
    세척the combined organic phases are washed six times with 100 ml of water
13. 13
    workup.ADDITIONSubsequently, 10 g of silica gel are added
14. 14
    workup.STIRRINGthe mixture is stirred for 1 hour
15. 15
    여과filtration
16. 16
    세척by washing three times
17. 17
    농축with 50 ml of toluene and concentration
18. 18
    기타by evaporation

실험 절차

5.77 g (78.96 mmol) of DMF are weighed into a 100 ml three-necked round-bottomed flask, equipped with a magnetic stirrer, thermometer, dropping funnel, reflux condenser and nitrogen delivery line, and cooled, with stirring, to 3° C. 12.11 g (78.96 mmol) of phosphorus oxychloride are then slowly added dropwise so that the internal temperature does not exceed 10° C. The reaction mixture is then heated to 80° C. and 10 g (39.48 mmol) of 3-(4-fluorophenyl)-1-isopropyl-1H-indole, dissolved in 10 ml of DMF, are added dropwise in the course of 30 min. Stirring is subsequently carried out for 1.5 hours at that temperature. Cooling and dilution with 10 ml of DMF are then carried out. The reaction mixture is transferred into a dropping funnel and, with stirring, slowly added dropwise at 40° C. to 10 g (0.25 mol) of sodium hydroxide in 200 ml of water. The aqueous phase is extracted four times with 50 ml of toluene and the combined organic phases are washed six times with 100 ml of water. Subsequently, 10 g of silica gel are added, the mixture is stirred for 1 hour and filtration is carried out, followed by washing three times with 50 ml of toluene and concentration by evaporation. 10.17 g of a brown oil are obtained, which is dissolved in 100 ml of hexane under reflux. 10 g of silica gel are added, and filtration is carried out while hot, followed by washing three times with 50 ml of hot hexane. The filtrate is concentrated by evaporation and the residue is recrystallised from 94% ethanol. Slightly beige crystals having a melting point of from 89.5 to 91° C. are obtained.

출처