Sodium hydride → Ethyl 4-chloro-6-(4-formylphenoxy)-1-methyl-2-indolecarboxylate

HRID 565050ノート

反応式

HRID 565050 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12].[H-].[Na+].F[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=1>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:21]2[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=2)[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:6]2[CH3:12]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 680234-FluorobenzaldehydeHCID 21194263Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate

生成物 1

HCID 21194191Ethyl 4-chloro-6-(4-formylphenoxy)-1-methyl-2-indolecarboxylate収率 64.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

After 1.00 g (3.94 mmol) of ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.16 g (3.94 mmol) of 60% sodium hydride and 30 ml of dimethylformamide, the suspension was stirred at room temperature until the mixture became an almost transparent solution. Then 0.54 g (4.34 mmol) of 4-fluoro-benzaldehyde was added to the solution at room temperature followed by stirring for 10 hours at 70° C. The reaction mixture was poured onto ice water. The resulting mixture was then extracted three times with ethyl acetate. The combined extracts were washed with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was isolated and purified by silica gel column chromatography to give 0.91 g (64.5%) of ethyl 4-chloro-6-(4-formylphenoxy)-1-methyl-2-indolecarboxylate.

後処理

  1. stirringby stirring for 10 hours at 70° C
  2. additionThe reaction mixture was poured onto ice water
  3. extractionThe resulting mixture was then extracted three times with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was isolated
  8. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-ea34c92f357e4de4896c01461489c2e5
出典データセット
uspto-grants-2001_01
特許番号
US06169107A

反応ノート

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