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

HRID 565040ノート

反応式

HRID 565040 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:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]([O:11][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-:29])=[O:28])[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 738951-Fluoro-2-nitrobenzeneHCID 21194263Ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate

生成物 1

HCID 21194137Ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate収率 94.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

After 0.42 g (1.64 mmol) of ethyl 4-chloro-6-hydroxy-1-methyl-2-indolecarboxylate was added to a suspension of 0.066 g (1.64 mmol) of 60% sodium hydride and 5 ml of dimethylformamide, the suspension was stirred at room temperature until the mixture became an almost transparent solution. Then 0.35 g (2.49 mmol) of 1-fluoro-2-nitrobenzene was added to the solution at room temperature followed by stirring for 5 hours at the same temperature. 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 0.53 g (94.3%) of ethyl 4-chloro-1-methyl-6-(2-nitrophenoxy)-2-indolecarboxylate.

後処理

  1. stirringby stirring for 5 hours at the same temperature
  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-bb4a6048ed284f78a01b609b5489867d
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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