Ethyl Acetate → 1H-Pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 2-ethyl ester

HRID 1272106ノート

反応式

HRID 1272106 の反応式
[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:9]2=[N:10][CH:11]=[C:12]([O:14]C(=O)C3C=CC=CC=3)[CH:13]=[C:8]2[CH:7]=1)=[O:5].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO>[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:23]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C:9]2=[N:10][CH:11]=[C:12]([OH:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 693563741H-Pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid, 5-(benzoyloxy)-, 1-(1,1-dimethylethyl) 2-ethyl ester

生成物 1

HCID 684243571H-Pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid, 5-hydroxy-, 1-(1,1-dimethylethyl) 2-ethyl ester収率 100%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2.20 g (5.36 mmol) 5-benzoyloxy pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester in 20 mL methanol was added 0.81 g (5.90 mmol) potassium carbonate. After 1 h the reaction was poured into ethyl acetate and extracted with 10% aqueous citric acid solution. The phases were separated and the organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:1) to give the product as a colourless oil (100%).

後処理

  1. extractionextracted with 10% aqueous citric acid solution
  2. customThe phases were separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:1)

出典と根拠

ORDレコード
ord-4da3d666d57745f0bf9a0345cdaa2c9f
出典データセット
uspto-grants-2007_04
特許番号
US07208494B2

反応ノート

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