Sodium hydride → 1H-Indole-5-carboxylic acid, 1-(2-methoxyethyl)-, methyl ester

HRID 2170849ノート

反応式

HRID 2170849 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH3:20]>O>[CH3:20][O:19][CH2:18][CH2:17][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 2737635methyl 1H-indole-5-carboxylate

生成物 1

HCID 671694841H-Indole-5-carboxylic acid, 1-(2-methoxyethyl)-, methyl ester収率 50%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of methyl 1H-indole-5-carboxylate (200 mg, 1.14 mmol) and sodium hydride (60% in oil, 39 mg, 1.71 mmol) in N,N-dimethylformanide (3 mL) was added 1-bromo-2-methoxyethane (190 mg, 1.37 mmol) at room temperature. Then the mixture was stirred at 60° C. for 2 hours. The mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL). The organic layer was washed with water (20 mL) and dried over sodium sulfate. After removal of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1) to give 132 mg (50%) of the title compound as colorless syrup.

後処理

  1. extractionextracted with ethyl acetate (20 mL)
  2. washThe organic layer was washed with water (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-6cb6d67f4d0b4e939f6ee6e390536e4f
出典データセット
uspto-grants-2015_06
特許番号
US09051296B2

反応ノート

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