Imidazole → 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2105328ノート

反応式

HRID 2105328 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].N1[CH:26]=[CH:25]N=C1.[Cl-].[NH4+]>CN(C)C=O>[CH2:25]([O:12][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([O:1][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20])=[CH:10][CH:9]=2)=[O:13])[CH3:26]

参加物

6

反応物 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 889585-Hydroxyindole-2-carboxylic acid

生成物 1

HCID 226767305-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester収率 98.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To the solution of 10.0 g (49.0 mmol) 5-hydroxyindole-2-carboxylic acid (commercially available) in 30 ml N,N-dimethylformamide, 7.7 g (51.1 mmol) tert-butyldimethylchlorosilane and 3.5 g (51.4 mmoL) imidazole was added. After 1 hour, the solution was poured on 10% aqueous ammonium chloride solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2 v/v) as eluant to give 15.3 g (98.5%) of the compound as a white solid.

後処理

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2 v/v) as eluant

出典と根拠

ORDレコード
ord-f873a1f4b3a745e4a728a1816f38f6ec
出典データセット
uspto-grants-2009_08
特許番号
US07579351B2

反応ノート

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