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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 453853
[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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(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%

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b221d243f2524303bc50d79c785b5aca
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08492559B2

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