Phosphorus oxychloride → HCID 23124897, 화합물

HRID 547974노트

반응식

HRID 547974 반응식
FC1C=CC(C2C3C(=CC=CC=3)N(C(C)C)C=2)=CC=1.P(Cl)(Cl)(Cl)=O.CO/C=C/C#N.C(=O)([O-])O.[Na+].[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([CH:52]([CH3:54])[CH3:53])[C:44]=2[CH:55]=[CH:56][C:57]#[N:58])=[CH:39][CH:38]=1>ClCCl>[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[N:45]([CH:52]([CH3:53])[CH3:54])[C:44]=2/[CH:55]=[CH:56]/[C:57]#[N:58])=[CH:39][CH:38]=1

참가 물질

7

반응물 5

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indoleHCID 53247133-MethoxyacrylonitrileHCID 67196878HCID 67196878, 화합물

생성물 1

HCID 23124897HCID 23124897, 화합물수율 45%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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%

후처리

  1. customInto a solution prepared
  2. customa reaction
  3. customfurther, the mixture was reacted for 6 hours at the reflux temperature
  4. customAfter completion of the reaction
  5. customthe reaction liquid
  6. extractionextracted with ethyl acetate three times
  7. washwashed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. filtrationThe magnesium sulfate was filtrated off
  10. concentrationthe resulting filtrate was concentrated
  11. customto obtain a concentrated residue
  12. additioncontaining mainly trans isomer)
  13. customThe resulting concentrated residue was purified by silica gel column chromatography (developing liquid: n-heptane/ethyl acetate: 10/1 to 5/1)

출처 및 근거

ORD 기록
ord-ca7c8a9825c94531adc834798246583a
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939674B2

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