Reaktion #10032

Reaktionsgleichung

water

acrolein

acrolein

3-(4-Fluorophenyl)-1-(1-Methylethyl)-1H-Indole

→

3-[3-(4-Fluorophenyl)-1-(1-Methylethyl)-1H-Indol-2-yl]-2-Propenal

Lösungsmittel

acetonitrile

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added dropwise in 30 minutes
2. 2
   Filtrationis filtered on Buchner
3. 3
   Waschenwashed with 75 ml of water
4. 4
   workup.DISSOLUTIONThe wet solid (49.7 g) is dissolved in toluene (250 ml)
5. 5
   workup.ADDITIONcelite (1 g) and charcoal (0.5 g) are added
6. 6
   workup.STIRRINGthe mixture is stirred at room temperature for 30 minutes
7. 7
   FiltrationAfter filtration of the solid
8. 8
   workup.DISTILLATIONthe solvent is distilled off at reduced pressure
9. 9
   workup.DISSOLUTIONthe residue is dissolved at 75° C. with isopropanol (72 ml)
10. 10
    TemperaturThe solution is cooled at 20° C.
11. 11
    workup.STIRRINGstirred at room temperature for 1 hour
12. 12
    FiltrationThe precipitate is filtered on Buchner
13. 13
    Waschenwashed twice with isopropanol (15 ml)
14. 14
    Sonstigedried at 60° C. under vacuum
15. 15
    Sonstige30.2 g (70% molar yield) of the product
16. 16
    Sonstigeare obtained

Vorschrift

Use of the crude acrolein coming from Example 3a. To a suspension of 3-[3-(4-Fluorophenyl)-1-(1-Methylethyl)-1H-Indole (35.8 g) phosphorus oxychloride (31.4 g) in acetonitrile (35 ml) cooled at 5° C. a solution of crude acrolein (32.3 g from Example 3a) in acetonitrile (40 ml) is added dropwise in 30 minutes. The reaction mixture is then warmed to 60° C. and kept under stirring at 60° C. for 4 hours; water (300 ml) is added and after 1 hour at 60° C. the formed solid is filtered on Buchner and washed with 75 ml of water. The wet solid (49.7 g) is dissolved in toluene (250 ml), celite (1 g) and charcoal (0.5 g) are added and the mixture is stirred at room temperature for 30 minutes. After filtration of the solid, the solvent is distilled off at reduced pressure and the residue is dissolved at 75° C. with isopropanol (72 ml). The solution is cooled at 20° C. and stirred at room temperature for 1 hour. The precipitate is filtered on Buchner, washed twice with isopropanol (15 ml) and dried at 60° C. under vacuum. 30.2 g (70% molar yield) of the product are obtained.

Quelle