Hexane → Dimethyl penta-2,3-dienedioate

HRID 505666노트

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HRID 505666 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 637810Dimethyl penta-2,3-dienedioate수율 40.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-fe72556c82164a3db3e5b6617def8470
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781485B2

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