Chloranil → Estra-4,6-diene-3,17-dione

HRID 1005308

Reaktionsgleichung

Reaktionsgleichung von HRID 1005308
[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH2:8][CH2:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][C:12](=[O:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20].C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.CCOC(C)=O.CCCCCC>C(O)C>[CH3:1][C@:2]12[CH2:18][CH2:17][C@H:16]3[C@@H:7]([CH:8]=[CH:9][C:10]4[C@@H:15]3[CH2:14][CH2:13][C:12](=[O:19])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:20]

Komponenten

5

Edukt 3

HCID 8371ChloranilHCID 92834(+)-Estr-4-ene-3,17-dioneHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 128845Estra-4,6-diene-3,17-dioneAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of dione 53 (5.0 g, 18.36 mmol) and chloranil (5.4 g, 22 mmol) in dry ethanol (500 mL) was stirred at 60-65° C. for 2 h. The reaction mixture was concentrated under reduced pressure, and the residue was triturated with dichloromethane. The solid was removed by filtration, and the filtrate was concentrated to give a brown gum. Chromatography (20% EtOAc/hexane) yielded crude dione 54 as a yellow solid (2.3 g, 46%): 1H NMR (300 MHz, CDCl3) δ 0.94 (s, 3, CH3), 5.78 (s, 1), 6.25 (m, 2).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was triturated with dichloromethane
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customto give a brown gum

Quellen und Nachweise

ORD-Eintrag
ord-5ff83862de1a4e38903d42971fb300e2
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06054446

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