Potassium Permanganate → HCID 59425724、化合物

HRID 252504ノート

反応式

HRID 252504 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:16]=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].[O-:18][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([C:16]([OH:18])=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4]

参加物

5

反応物 2

HCID 516875Potassium Permanganate2 回HCID 59425156Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate

生成物 1

HCID 59425724HCID 59425724、化合物収率 80.4%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒2 回

実験手順

1-Ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester (800 mg, 3.5 mmol), prepared as shown in example 1P, step A, is dissolved in acetone (98 mL). A solution of KMnO4 (655 mg, 4.15 mmol) in H2O (31 mL) is added. The reaction mixture is stirred at room temperature for 90 minutes. Another addition of KMnO4 (108 mg) in H2O (6 mL), followed by stirring for another 45 minutes is required to drive the reaction to completion. The reaction mixture is then quenched with 10% H2O2 (1.5 mL). The mixture is filtered through celite. The filtrate is stripped down under vacuum to roughly ⅓ of the volume. The residue is acidified with 6N HCl, and is extracted into ethyl acetate. The solids isolated from the ethyl acetate layer are triturated with acetone to yield 1-ethyl-1H-indole-3,6-dicarboxylic acid 6-methyl ester (696 mg, 79%) as a light orange solid.

後処理

  1. stirringby stirring for another 45 minutes
  2. customthe reaction to completion
  3. customThe reaction mixture is then quenched with 10% H2O2 (1.5 mL)
  4. filtrationThe mixture is filtered through celite
  5. extractionis extracted into ethyl acetate
  6. customThe solids isolated from the ethyl acetate layer
  7. customare triturated with acetone

出典と根拠

ORDレコード
ord-26e6c966e2104b02b004fe2b38a8d990
出典データセット
uspto-grants-2011_01
特許番号
US07868037B2

反応ノート

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