Hexane → Dimethyl penta-2,3-dienedioate

HRID 505666Notes

Reaction equation

HRID 505666 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-fe72556c82164a3db3e5b6617def8470
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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