HCID 57698807, Verbindung → HCID 67166341, Verbindung

HRID 552377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552377
[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:2]=[CH2:3]>C(O)(=O)C.C(O)C.C(OCC)(=O)C.[Fe]>[CH2:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:5]=1[C:6]([O:8][CH3:9])=[O:7])[CH:2]=[CH2:3]

Komponenten

6

Edukt 1

HCID 57698807HCID 57698807, Verbindung

Produkt 1

HCID 67166341HCID 67166341, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred suspension of Step 1 intermediate (4.2 g, 19.98 mmol) in a mixture of 50% aqueous acetic acid (100 ml) and ethanol (100 ml) was added iron powder (5.3 g, 99.9 g atom) and the mixture was refluxed for 3 h. The mixture was cooled to room temperature and filtered through a celite bed. The filtrate was concentrated and the residue obtained was diluted with ethyl acetate and washed with water (2×50 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated to give 3.2 g of the product as a brown oil; 1H NMR (δ ppm, CDCl3, 300 MHz): 7.15-7.07 (m, 1H); 6.62-6.55 (m, 2H); 5.99-5.82 (m, 1H); 5.05-4.95 (m, 2H); 3.86 (s, 3H); 3.53 (d, J=6.0, 2H).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationfiltered through a celite bed
  3. concentrationThe filtrate was concentrated
  4. customthe residue obtained
  5. washwashed with water (2×50 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-bd5b187a8b694de4972d74254a8c8132
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951814B2

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