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

HRID 2357016

反応式

HRID 2357016 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24611Copper bromide (CuBr2)触媒HCID 887Methanol溶媒HCID 8058Hexane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7641ae064db54c19a66a9d5904327093
出典データセット
uspto-grants-2010_07
特許番号
US07759399B2

関連ノート

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