Ethyl 1-phenylindole-3-glyoxylate → Ethyl 1-phenylindole-3-acetate

HRID 863545

Reaktionsgleichung

Reaktionsgleichung von HRID 863545
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Ni].C(O)C.O>[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 1

HCID 54522388Ethyl 1-phenylindole-3-glyoxylate

Produkt 1

HCID 53656737Ethyl 1-phenylindole-3-acetateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 10 g (34.1 mmol) of ethyl 1-phenylindole-3-glyoxylate and about 25 g of Raney nickel in 350 ml of ethanol and 150 ml of water was heated at reflux for 6 hours. The suspension was filtered through glass fiber filter paper and the solid was washed with four 50 ml portions of ethyl acetate while taking care not to allow the solid to dry. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel using ethyl acetate/hexane (1:2) for the elution. There were obtained 6.38 g of ethyl 1-phenylindole-3-acetate as a yellow oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. filtrationThe suspension was filtered through glass fiber
  4. filtrationfilter paper
  5. washthe solid was washed with four 50 ml portions of ethyl acetate
  6. customto dry
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by flash chromatography on silica gel
  9. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-052a9b0004794719bfc5d802cd3b4306
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05721230

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