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Hydrochloric Acid → ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate

HRID 38490
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 38490
[CH:1]1([N:4]2[CH:8]=[CH:7][CH:6]=[C:5]2[CH:9]=O)[CH2:3][CH2:2]1.[C:11]([O:20][CH2:21][CH3:22])(=O)[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].Cl.CC([O-])=[O:26].[K+]>CCO.C(OC(=O)C)(=O)C>[C:21]([O:20][C:11]1[CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=[C:5]2[C:6]=1[CH:7]=[CH:8][N:4]2[CH:1]1[CH2:2][CH2:3]1)(=[O:26])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 31249Diethyl SuccinateHCID 517044Potassium AcetateHCID 434769981-cyclopropyl-1H-pyrrole-2-carbaldehyde

Produkt 1

HCID 57930960ethyl 4-acetoxy-1-cyclopropyl-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
2×
HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Na (14.6 g) was added portion wise to EtOH (400 ml) with stirring at room temperature. To the mixture was added a solution of 1-cyclopropyl-1H-pyrrole-2-carbaldehyde (38.9 g) and diethyl succinate (48.2 ml) in EtOH (100 ml) at 50° C., then the mixture was refluxed overnight. 140 ml of aqueous 5N HCl was added to the mixture at 0° C. and EtOH was evaporated. The residue was extracted with CHCl3, the organic layer was dried over Na2SO4 and concentrated to give red oil. The material was dissolved in 400 ml of acetic anhydride and KOAc (47.4 g) was added thereto. The mixture was refluxed for 30 min. and allowed to cool to room temperature. The mixture was filtrated and the filtrate was concentrated. The residue was purified by silicagel column chromatography (hexane/EtOAc) to give intended compound a red oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed overnight
  2. customEtOH was evaporated
  3. extractionThe residue was extracted with CHCl3
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give red oil
  7. temperatureThe mixture was refluxed for 30 min.
  8. temperatureto cool to room temperature
  9. filtrationThe mixture was filtrated
  10. concentrationthe filtrate was concentrated
  11. customThe residue was purified by silicagel column chromatography (hexane/EtOAc)
  12. customto give

Quellen und Nachweise

ORD-Eintrag
ord-0f616e70cc5c40efbc4a893598adad59
Quelldatensatz
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08524730B2

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