Diethyl Ether → 2,2-Dimethylcyclopent-4-ene-1,3-dione

HRID 2357016

Reaktionsgleichung

Reaktionsgleichung von HRID 2357016
[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].C(OCC)C>CO.CCCCCC.[Cu](Br)Br>[CH3:1][C:2]1([CH3:9])[C:6](=[O:7])[CH:5]=[CH:4][C:3]1=[O:8]

Komponenten

6

Edukt 2

HCID 3283Diethyl EtherHCID 197631,3-Cyclopentanedione, 2,2-dimethyl-

Produkt 1

HCID 45746952,2-Dimethylcyclopent-4-ene-1,3-dioneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24611Copper bromide (CuBr2)KatalysatorHCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Copper (II) bromide (63.4 g, 0.28 mol) was added to a stirred solution of the dione 2 (17.9 g, 0.14 mol) in methanol (280 ml) at room temperature, under an atmosphere of nitrogen. The reaction was heated under reflux for 90 minutes and then cooled to room temperature. The mixture was then filtered through celite, washing with dichloromethane (3×250 ml) and evaporated in vacuo. Flash chromatography (SiO2, 50% diethyl ether in hexane) gave the enedione 3 (11.3 g, 91.0 mmol, 64%) as a yellow oil; δH (300 MHz, CDCl3) 7.22 (2H, s, CH═CH), 1.17 (3H, s, CH3), 1.15 (3H, s, CH3); δC (75.5 MHz, CDCl3) 207.7 (s), 147.1 (d), 46.4 (s), 19.5 (q).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 90 minutes
  3. filtrationThe mixture was then filtered through celite
  4. washwashing with dichloromethane (3×250 ml)
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7641ae064db54c19a66a9d5904327093
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759399B2

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