Реакция #731286

Уравнение реакции

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

Выход 45.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеInto a solution prepared
2. 2
   Другоеa reaction
3. 3
   Другоеfurther, the mixture was reacted for 6 hours at the reflux temperature
4. 4
   ДругоеAfter completion of the reaction
5. 5
   Другоеthe reaction liquid
6. 6
   Экстракцияextracted with ethyl acetate three times
7. 7
   Промывкаwashed with water
8. 8
   Сушкаdried with anhydrous magnesium sulfate
9. 9
   ФильтрацияThe magnesium sulfate was filtrated off
10. 10
    Концентрированиеthe resulting filtrate was concentrated
11. 11
    Другоеto obtain a concentrated residue
12. 12
    workup.ADDITIONcontaining mainly trans isomer)
13. 13
    ДругоеThe resulting concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate: 10/1 to 5/1)

Методика

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%

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