Ethyl pyruvate → 4,6-di-tert-butyl-1H-indole-2-carboxylic acid ethyl ester

HRID 513854

反応式

HRID 513854 の反応式
C(=N[NH:15][C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:19]=[C:18]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:17]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:30]([O:35][CH2:36][CH3:37])(=[O:34])[C:31]([CH3:33])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)C.O>[CH2:36]([O:35][C:30]([C:31]1[NH:15][C:16]2[C:17]([CH:33]=1)=[C:18]([C:26]([CH3:27])([CH3:28])[CH3:29])[CH:19]=[C:20]([C:22]([CH3:25])([CH3:23])[CH3:24])[CH:21]=2)=[O:34])[CH3:37]

参加物

7

反応物 4

HCID 12041Ethyl pyruvateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86669219N-benzhydrylidene-N'-(3,5-di-tert-butyl-phenyl)-hydrazine

生成物 1

HCID 680050974,6-di-tert-butyl-1H-indole-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

N-Benzhydrylidene-N′-(3,5-di-tert-butyl-phenyl)-hydrazine (617 mg, 1.6 mmol) was dissolved in ethanol (12 ml). Then, ethyl pyruvate (212 μl, 1.9 mmol) and p-toluene sulfonic acid monohydrate (914 mg, 4.8 mmol) were added thereto. This was heated and stirred at 150° C. by microwave under a nitrogen atmosphere for one hour. After cooling it to room temperature, the reaction mixture was combined with water and an aqueous solution saturated with sodium bicarbonate. The product was extracted into ethyl acetate. The organic layer was isolated, and washed with an aqueous solution saturated with sodium chloride, and dried over magnesium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate=100/5). Thus, 4,6-di-tert-butyl-1H-indole-2-carboxylic acid ethyl ester was obtained as a brown solid (268 mg, 56%).

後処理

  1. temperatureThis was heated
  2. temperatureAfter cooling it to room temperature
  3. extractionThe product was extracted into ethyl acetate
  4. customThe organic layer was isolated
  5. washwashed with an aqueous solution saturated with sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe desiccant was removed by filtration, and concentration
  8. customThen, the residue obtained by concentration under reduced pressure
  9. customwas purified by silica gel column chromatography (hexane/ethyl acetate=100/5)

出典と根拠

ORDレコード
ord-b78d395599444a72b35c895ac6dfd685
出典データセット
uspto-grants-2015_08
特許番号
US09102692B2

関連ノート

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