반응 #635156

반응 방정식

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

수율 45.0%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타Into a solution prepared
2. 2
   기타a reaction
3. 3
   기타further, the mixture was reacted for 6 hours at the reflux temperature
4. 4
   기타After completion of the reaction
5. 5
   기타the reaction liquid
6. 6
   추출extracted with ethyl acetate three times
7. 7
   세척washed with water
8. 8
   건조dried with anhydrous magnesium sulfate
9. 9
   여과The magnesium sulfate was filtrated off
10. 10
    농축the resulting filtrate was concentrated
11. 11
    기타to obtain a concentrated residue
12. 12
    workup.ADDITIONcontaining mainly trans isomer)
13. 13
    기타The resulting concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate: 10/1 to 5/1)

실험 절차

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%

출처