Piperidine → 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde

HRID 555659ノート

反応式

HRID 555659 の反応式
C([C:3]1[CH:7]=[CH:6][O:5][C:4]=1[CH:8]=[O:9])=O.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=O.N1CCCC[CH2:21]1>C(O)C>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)/[C:12](=[CH:21]\[C:6]2[O:5][C:4]([CH:8]=[O:9])=[CH:3][CH:7]=2)/[CH2:11]1

参加物

5

反応物 3

HCID 8082PiperidineHCID 321710OxindoleHCID 13814199Furan-2,3-dicarbaldehyde

生成物 1

HCID 866402795-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde収率 31%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Diformylfuran (1 equivalent) was dissolved in ethanol, and a solution obtained by dissolving oxindole (0.5 equivalent) and piperidine (0.1 equivalent) in ethanol was gradually added thereto. After completion of the addition, the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the resulting precipitate was removed by filtration. To the filtrate, acetone was added and the resulting solution was acidified with a 1 N hydrochloric acid solution and evaporated to dryness under reduced pressure, whereby 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde was obtained (yield: 31%). Subsequently, the thus obtained 5-((E)-(indolin-3-ylidene)methyl)furan-2-carbaldehyde (1.2 equivalents), 1-acetyloxindole (1 equivalent) and piperidine (0.1 equivalent) were dissolved in ethanol and the resulting mixture was stirred at room temperature for 12 hours. After completion of the reaction, the resulting precipitate was collected by filtration, washed with cooled ethanol and dried, whereby a target compound was obtained.

後処理

  1. customa solution obtained
  2. additionwas gradually added
  3. additionAfter completion of the addition
  4. customAfter completion of the reaction
  5. customthe resulting precipitate was removed by filtration
  6. additionTo the filtrate, acetone was added
  7. customevaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-8f1430175c1540e4a4ec910257ce75e3
出典データセット
uspto-grants-2011_11
特許番号
US08053461B2

反応ノート

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