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

HRID 9938
ノート
印刷プレビュー

反応式

HRID 9938 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 7847Acrolein2 回HCID 24813Phosphorus oxychlorideHCID 7362293-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile
溶媒
2 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3f435dfa66004070964eaa59ec28607f
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07091382B2

反応ノート

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