Imidazole → 6-Chloro-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

HRID 1724615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1724615
N1C=CN=C1.[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[O:17]C(=O)C)[O:13][CH2:12][CH:11]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C(=O)C)=[CH:23][CH:22]=1)[C:10]2=[O:31]>C(O)C>[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][C:16]=1[OH:17])[O:13][CH2:12][CH:11]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:10]2=[O:31]

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 9842545HCID 9842545, Verbindung

Produkt 1

HCID 99260276-Chloro-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneAusbeute 802,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Imidazole (0.60 g) was added to a suspension of 6-chloro-4′,7-diacetoxyisoflavan-4-one (0.24 g, 0.06 mmol) in absolute ethanol (5.0 ml) and the mixture was refluxed for 45 min under argon. The solution was concentrated under reduced pressure and distilled water (10 ml) was added to the residue. The mixture was left overnight in the fridge and the resulting precipitate was filtered, washed with water and dried to yield 6-chloro-4′,7-dihydroxyisoflavan-4-one (0.14 g, 75%) as a white powder. 1H NMR (d6-acetone): δ 3.87 (t, 1H, J 7.2 Hz, H3), 4.64 (d, 2H, J 6.2 Hz, H2), 6.59 (s, 1H, H8), 6.78 (d, 2H, J 8.7 Hz, ArH), 7.10 (d, 2H, J 8.7 Hz, ArH), 7.70 (bs, 1H, OH), 7.77 (s, 1H, H5).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 45 min under argon
  2. concentrationThe solution was concentrated under reduced pressure
  3. distillationdistilled water (10 ml)
  4. additionwas added to the residue
  5. filtrationthe resulting precipitate was filtered
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c65eb4a3aa1e43cfa4d65f4bf0d2aef4
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07488494B2

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