Water → 9-ethyl-9H-carbazole-3,6-dicarbaldehyde

HRID 1378964

反応式

HRID 1378964 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:9]1[C:21]2[CH:20]=[CH:19][C:18]([C:22](O)=[O:23])=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[C:13]([C:25](O)=[O:26])[CH:14]=2)[CH3:8].[H-].O>C1COCC1.ClCCl.[O-2].[O-2].[Mn+4]>[CH:25]([C:13]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:7][CH3:8])[C:21]3[C:16]([C:15]=2[CH:14]=1)=[CH:17][C:18]([CH:22]=[O:23])=[CH:19][CH:20]=3)=[O:26]

参加物

8

反応物 4

HCID 962WaterHCID 166653HydrideHCID 37979149-ethyl-9H-carbazole-3,6-dicarboxylic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 37166759-ethyl-9H-carbazole-3,6-dicarbaldehyde

試薬・触媒・溶媒 3

HCID 178418406HCID 178418406、化合物触媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

LiAlH4 (2.15 g, 56.3 mmol) is added portionwise to a suspension of N-ethylcarbazole-3,6-dicarboxylic acid (5.7 g, 20.12 mmol) in 160 ml of anhydrous THF cooled to 0° C. The suspension is stirred for 1 h 30 min at room temperature and then 1 hour under reflux. After cooling to 0° C., the excess hydride is hydrolyzed with a little water and the salts are filtered off. The filtrate is evaporated to dryness and dried under vacuum to give a yellow solid. The latter is suspended in dichloromethane in the presence of activated manganese dioxide (4 g, 15.16 mmol), and the mixture is stirred overnight at room temperature. 4 g of activated manganese dioxide are added and the mixture is stirred for a further 24 h. The suspension is filtered and the filtrate is evaporated under vacuum to give the expected product.

後処理

  1. temperature1 hour under reflux
  2. temperatureAfter cooling to 0° C.
  3. filtrationthe salts are filtered off
  4. customThe filtrate is evaporated to dryness
  5. customdried under vacuum
  6. customto give a yellow solid
  7. stirringthe mixture is stirred overnight at room temperature
  8. stirringthe mixture is stirred for a further 24 h
  9. filtrationThe suspension is filtered
  10. customthe filtrate is evaporated under vacuum

出典と根拠

ORDレコード
ord-e00299b5658d48bd9d89bd319d5dee5b
出典データセット
uspto-grants-1997_09
特許番号
US05670493

関連ノート

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