Reaktion #635156

Reaktionsgleichung

sodium hydrogen carbonate

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

phosphorus oxychloride

3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylonitrile

trans-3-methoxyacrylonitrile

→

trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylonitrile

Ausbeute 45.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a solution prepared
2. 2
   Sonstigea reaction
3. 3
   Sonstigefurther, the mixture was reacted for 6 hours at the reflux temperature
4. 4
   SonstigeAfter completion of the reaction
5. 5
   Sonstigethe reaction liquid
6. 6
   Extraktionextracted with ethyl acetate three times
7. 7
   Waschenwashed with water
8. 8
   Trocknendried with anhydrous magnesium sulfate
9. 9
   FiltrationThe magnesium sulfate was filtrated off
10. 10
    Einengenthe resulting filtrate was concentrated
11. 11
    Sonstigeto obtain a concentrated residue
12. 12
    workup.ADDITIONcontaining mainly trans isomer)
13. 13
    SonstigeThe resulting concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate: 10/1 to 5/1)

Vorschrift

Into a solution prepared by dissolving 0.63 g of 3-(4-fluorophenyl)-1-isopropyl-1H-indole in 3 mL of dichloromethane was added dropwise 0.77 g of phosphorus oxychloride at an inner temperature of 0 to 10° C., then, 0.92 g of trans-3-methoxyacrylonitrile was added dropwise. Then, the mixture was stirred overnight at room temperature to cause a reaction, further, the mixture was reacted for 6 hours at the reflux temperature. After completion of the reaction, the reaction liquid was added into 100 mL of 5 wt % aqueous sodium hydrogen carbonate, and extracted with ethyl acetate three times. The resulting organic layers were combined and washed with water, then, dried with anhydrous magnesium sulfate. The magnesium sulfate was filtrated off, and the resulting filtrate was concentrated to obtain a concentrated residue containing 3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylonitrile (trans-cis isomer mixture containing mainly trans isomer). The resulting concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate: 10/1 to 5/1) to obtain 0.34 g of trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylonitrile (yellow solid). Yield: 45%

Quelle