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(E)-Methyl 2-(2-chloro-6-nitrophenyl)-3-hydroxybut-2-enoate → methyl 4-chloro-2-methyl-1H-indole-3-carboxylate

HRID 453853
ノート
印刷プレビュー

反応式

HRID 453853 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1/[C:11](=[C:16](\O)/[CH3:17])/[C:12]([O:14][CH3:15])=[O:13]>C(O)(=O)C.O.C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:16]([CH3:17])[NH:8]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 1

HCID 86761957(E)-Methyl 2-(2-chloro-6-nitrophenyl)-3-hydroxybut-2-enoate

生成物 1

HCID 59473719methyl 4-chloro-2-methyl-1H-indole-3-carboxylate収率 91%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
90 °C

実験手順

(E)-Methyl 2-(2-chloro-6-nitrophenyl)-3-hydroxybut-2-enoate (14.76 mmol, 1.0 equiv.) was dissolved in acetic acid (96 ml), and a solution of TiCl3 (20%-w/w in 2 N HCl, 71.6 ml) was added, with stirring. The mixture was then heated for 5-10 min at 90° C. The reaction mixture was cooled with an ice bath and diluted with water and DCM/methanol (9:1, 100 ml). The phases were separated and the organic phase was washed with water and sat. NaCl solution. Drying over Na2SO4 was then carried out, followed by concentration under reduced pressure. The product was crystallized from hexane. Yield: 91%

後処理

  1. temperatureThe reaction mixture was cooled with an ice bath
  2. customThe phases were separated
  3. washthe organic phase was washed with water and sat. NaCl solution
  4. dry with materialDrying over Na2SO4
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe product was crystallized from hexane

出典と根拠

ORDレコード
ord-b221d243f2524303bc50d79c785b5aca
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492559B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート