Pyrrolidine → (3Z)-3-(((4Z,6Z,8E)-azulen-1-yl)methylene)-5-phenylindolin-2-one

HRID 2236124ノート

反応式

HRID 2236124 の反応式
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][C:11](=[O:16])[CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH:27]=O)[C:26]2[C:20]([CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:19][CH:18]=1.N1CCCC1>C(O)C>[C:17]1(/[CH:27]=[C:10]2\[C:11](=[O:16])[NH:12][C:13]3[C:9]\2=[CH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][CH:14]=3)=[CH:18][CH:19]=[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=[C:26]12

参加物

5

反応物 3

HCID 31268PyrrolidineHCID 117448701-Azulene carboxyaldehydeHCID 133019785-Phenyloxindole

生成物 1

HCID 59301667(3Z)-3-(((4Z,6Z,8E)-azulen-1-yl)methylene)-5-phenylindolin-2-one収率 22.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

0.4389 g 5-phenyloxindole (0.0021 mole) and 0.323 g azulene aldehyde (0.0021 mole) were dissolved in 30 mL dried ethanol. 1.5 mL pyrrolidine (1M) was then added and uniformly stirred at reflux temperature for two hours. After removal of dried ethanol, the results were extracted by dichloromethane and citric acid aqueous solution. The organic layer was collected, dried with anhydrous magnesium sulfate, filtered, concentrated under vacuum, and separated by silica gel column chromatography to give Z-form Compound 034 (0.1621 g).

後処理

  1. temperatureat reflux temperature for two hours
  2. customAfter removal of dried ethanol
  3. extractionthe results were extracted by dichloromethane and citric acid aqueous solution
  4. customThe organic layer was collected
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customseparated by silica gel column chromatography

出典と根拠

ORDレコード
ord-d6dd7afe5b17411d803f1f4e5aa4aa26
出典データセット
uspto-grants-2010_05
特許番号
US07714146B2

反応ノート

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