Reaktion #10034

Reaktionsgleichung

acrolein

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

phosphorus oxychloride

acrolein

water

→

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 60 minutes
2. 2
   Filtrationis filtered on Buchner
3. 3
   Waschenwashed with water (250 ml×3)
4. 4
   workup.DISSOLUTIONThe wet solid (131 g) is dissolved in toluene (1050 ml)
5. 5
   workup.ADDITIONcelite (2.7 g) and charcoal (4 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
   Waschenthe mixture is washed with water (500 ml×2)
9. 9
   Sonstigethe phases are separated
10. 10
    workup.DISTILLATIONthe organic solvent is distilled off at reduced pressure
11. 11
    workup.DISSOLUTIONthe residue is dissolved at 75° C. with isopropanol (260 ml)
12. 12
    TemperaturThe solution is cooled at 10° C.
13. 13
    workup.STIRRINGstirred for 1 hour
14. 14
    FiltrationThe precipitate is filtered on Buchner
15. 15
    Waschenwashed with isopropanol (60 ml×3)
16. 16
    Sonstigedried at 60° C. under vacuum
17. 17
    Sonstige84.2 g (53% molar yield) of the product
18. 18
    Sonstigeare obtained

Vorschrift

Use of the crude acrolein coming from Example 4a. To a suspension of 3-[3-(4-Fluorophenyl)-1-(1-Methylethyl)-1H-Indole (130.7 g), phosphorus oxychloride (114.6 g) in acetonitrile (128 ml) cooled at 5° C. a solution of crude acrolein (116.9 g from Example 4a) in acetonitrile (145 ml) is added dropwise in 60 minutes. The reaction mixture is then warmed to 60° C. and kept under stirring at 60° C. for 6 hours; water (1100 ml) is added and after 1 hour at 60° C. the formed solid is filtered on Buchner and washed with water (250 ml×3). The wet solid (131 g) is dissolved in toluene (1050 ml), celite (2.7 g) and charcoal (4 g) are added and the mixture is stirred at room temperature for 30 minutes. After filtration of the solid, the mixture is washed with water (500 ml×2), the phases are separated, the organic solvent is distilled off at reduced pressure and the residue is dissolved at 75° C. with isopropanol (260 ml). The solution is cooled at 10° C. and stirred for 1 hour. The precipitate is filtered on Buchner, washed with isopropanol (60 ml×3) and dried at 60° C. under vacuum. 84.2 g (53% molar yield) of the product are obtained.

Quelle