4-Methoxy-3-hydroxy-2-nitrobutyric acid ethyl ester → 3-(4-Acetoxymethylindol-3-yl)-2-nitro-4-methoxy-butyric acid ethyl ester

HRID 569078

反応式

HRID 569078 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2)(=[O:3])[CH3:2].[CH2:15]([O:17][C:18](=[O:28])[CH:19]([N+:25]([O-:27])=[O:26])[CH:20](O)[CH2:21][O:22][CH3:23])[CH3:16]>C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:15]([O:17][C:18](=[O:28])[CH:19]([N+:25]([O-:27])=[O:26])[CH:20]([C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[CH:14][C:6]=2[CH2:5][O:4][C:1](=[O:3])[CH3:2])[NH:10][CH:9]=1)[CH2:21][O:22][CH3:23])[CH3:16]

参加物

5

反応物 2

HCID 131339864-Methoxy-3-hydroxy-2-nitrobutyric acid ethyl esterHCID 201323834-Acetoxymethylindole

生成物 1

HCID 542935723-(4-Acetoxymethylindol-3-yl)-2-nitro-4-methoxy-butyric acid ethyl ester

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 1140Toluene溶媒

実験手順

4-Acetoxymethylindole (189 g) is dissolved in a mixture of toluene (6 l) and acetic acid (0.7 l). To this solution is added 3-hydroxy-2-nitro-5-oxa-hexanoic acid ethyl ester (570 ml). The flask containing the mixture is evacuated by means of a water jet pump. Then balancing to normal pressure is brought about by argon. Evacuation and pressure balancing are repeated four times. Then the reaction mixture is refluxed for two hours in a water-free argon atmosphere. After concentrating to 2 l the solution is diluted with ethyl acetate and shaken out three times with a liter of 1N hydrochloric acid each. Then it is washed to neutrality with saturated hydrochloric acid solution. The solution, dried over sodium sulfate, is evaporated. The residue is chromatographed on silica gel with dicloromethane. 393 g of the title compound is obtained in oily form.

後処理

  1. additionThe flask containing the mixture
  2. customis evacuated by means of a water jet pump
  3. temperatureThen the reaction mixture is refluxed for two hours in a water-free argon atmosphere
  4. concentrationAfter concentrating to 2 l the solution
  5. additionis diluted with ethyl acetate
  6. washThen it is washed to neutrality with saturated hydrochloric acid solution
  7. dry with materialThe solution, dried over sodium sulfate
  8. customis evaporated
  9. customThe residue is chromatographed on silica gel with dicloromethane

出典と根拠

ORDレコード
ord-28aff600685b425abcbf35c0ea92f9de
出典データセット
uspto-grants-1988_03
特許番号
US04731365

関連ノート

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