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

HRID 2357016

반응식

HRID 2357016 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24611Copper bromide (CuBr2)촉매HCID 887Methanol용매HCID 8058Hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7641ae064db54c19a66a9d5904327093
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07759399B2

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