Imidazole → 3(2H)-Isoflavene

HRID 603280Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 603280
N1C=CN=C1.C(O[C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[C:15]([C:20]3[CH:25]=[CH:24][C:23](OC)=[CH:22][CH:21]=3)[CH2:16][O:17]2)=[CH:12][CH:11]=1)(=O)C>C(O)C>[O:17]1[C:18]2[C:13](=[CH:12][CH:11]=[CH:10][CH:19]=2)[CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16]1

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 264550MLS002703491

Produkt 1

HCID 5004603(2H)-Isoflavene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Imidazole (0.18 g) was added to a suspension of 7-acetoxy-4′-methoxyisoflav-3-ene (0.06 g, 0.02 mmol) in absolute ethanol (5.0 ml) and the mixture was refluxed for 45 minutes under argon. The solution was concentrated under reduced pressure and the product was precipitated by addition of distilled water (10 ml). The mixture was left overnight in the fridge and filtered to yield isoflav-3-ene. The crude product was recrystallised from methanol/benzene to yield 7-hydroxy-4′-methoxyisoflav-3-ene (0.034 g, 66%). 1H NMR (CDCl3+d6-DMSO): δ 3.74 (s, 3H, OCH3), 4.99 (s, 2H, H2), 6.21 (d, 1H, J 2.3 Hz, H8), 6.29 (dd, 1H, J 2.3 Hz, 8.3 Hz, H6), 6.67 (bs, 1H, H4), 6.85 (d, 1H, J 8.3 Hz, H5), 6.86 (d, 2H, J 8.7 Hz, ArH), 7.33 (d, 2H, J 8.7 Hz, ArH).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 45 minutes under argon
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe product was precipitated by addition of distilled water (10 ml)
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-107dd5d8e21a43ffad44953eab33cd2c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906660B2

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