Hexane → Dimethyl penta-2,3-dienedioate

HRID 505666ノート

反応式

HRID 505666 の反応式
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5](=O)[CH2:6][C:7]([O:9][CH3:10])=[O:8].[Cl-].ClC1N(C)C=C[N+]=1C.C(N(CC)CC)C.CCCCCC>ClCCl.O>[CH3:10][O:9][C:7](=[O:8])[CH:6]=[C:5]=[CH:4][C:3]([O:2][CH3:1])=[O:12]

参加物

7

反応物 4

HCID 8058HexaneHCID 8471TriethylamineHCID 74591Dimethyl 3-oxoglutarateHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chloride

生成物 1

HCID 637810Dimethyl penta-2,3-dienedioate収率 40.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

3-Oxopentanedioic acid dimethyl ester (11 mL, 75 mmol) was dissolved in dichloromethane (100 mL), and cooled to 0° C. The obtained solution was added with 2-chloro-1,3-dimethylimidazolium chloride (14 g, 83 mmol) and triethylamine (31 mL, 0.23 mol), warmed up to a room temperature and stirred for 4 hours. The reaction mixture was added with hexane (200 mL) and water and extracted with hexane 3 times. The organic layers were combined and sequentially washed with water and saturated brine, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain penta-2,3-dienedioic acid dimethyl ester (4.7 g, 40%).

後処理

  1. temperaturewarmed up to a room temperature
  2. extractionextracted with hexane 3 times
  3. washsequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-fe72556c82164a3db3e5b6617def8470
出典データセット
uspto-grants-2010_08
特許番号
US07781485B2

反応ノート

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