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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
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HRID 453853 반응식
[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
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참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
90 °C

실험 절차

(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%

후처리

  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

출처 및 근거

ORD 기록
ord-b221d243f2524303bc50d79c785b5aca
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492559B2

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