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Water → 3-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-YL]-2-propenal

HRID 9938
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HRID 9938 반응식
[CH:1]([CH:3]=[CH2:4])=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH:21]([CH3:23])[CH3:22])[CH:13]=2)=[CH:8][CH:7]=1.P(Cl)(Cl)(Cl)=O.O>C(#N)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH:21]([CH3:23])[CH3:22])[C:13]=2[CH:4]=[CH:3][CH:1]=[O:2])=[CH:8][CH:7]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 7847Acrolein2회HCID 24813Phosphorus oxychlorideHCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole

생성물 1

HCID 533952913-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-YL]-2-propenal

시약·촉매·용매 1

HCID 6342Acetonitrile
용매
2회

반응 조건

온도
60 °C

실험 절차

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.

후처리

  1. additionis added dropwise in 60 minutes
  2. filtrationis filtered on Buchner
  3. washwashed with water (250 ml×3)
  4. dissolutionThe wet solid (131 g) is dissolved in toluene (1050 ml)
  5. additioncelite (2.7 g) and charcoal (4 g) are added
  6. stirringthe mixture is stirred at room temperature for 30 minutes
  7. filtrationAfter filtration of the solid
  8. washthe mixture is washed with water (500 ml×2)
  9. customthe phases are separated
  10. distillationthe organic solvent is distilled off at reduced pressure
  11. dissolutionthe residue is dissolved at 75° C. with isopropanol (260 ml)
  12. temperatureThe solution is cooled at 10° C.
  13. stirringstirred for 1 hour
  14. filtrationThe precipitate is filtered on Buchner
  15. washwashed with isopropanol (60 ml×3)
  16. customdried at 60° C. under vacuum
  17. custom84.2 g (53% molar yield) of the product
  18. customare obtained

출처 및 근거

ORD 기록
ord-3f435dfa66004070964eaa59ec28607f
출처 데이터셋
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07091382B2

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