Dimethylformamide → Diallyl bis{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate

HRID 1015928Notes

Reaction equation

HRID 1015928 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].[C:7]([O:16][CH2:17][CH:18]=[CH2:19])(=[O:15])[CH2:8][C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10].I[CH2:21][CH2:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1.CN([CH:36]=[O:37])C>>[CH3:30][O:29][C:27]([C:26]1[CH:31]=[CH:32][C:23]([CH2:22][CH2:21][C:8]([CH2:21][CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:1]([O:37][CH3:36])=[O:4])=[CH:25][CH:24]=2)([C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10])[C:7]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])=[CH:24][CH:25]=1)=[O:28]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 228227Diallyl malonateHCID 22639144Methyl 4-(2-iodoethyl)benzoate

Product 1

HCID 59397503Diallyl bis{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate

Procedure

At room temperature, 61.9 g (190.02 mmol) of cesium carbonate are added to a solution of 10 g (54.3 mmol) of diallyl malonate and 47.25 g (purity 80%, 130.3 mmol) of methyl 4-(2-iodoethyl)benzoate in 100 ml DMF, and the mixture is then stirred at room temperature overnight. After the reaction has gone to completion, the reaction solution is evaporated to dryness and the residue is taken up in 100 ml of water and 100 ml of diethyl ether. The aqueous phase is extracted five times with diethyl ether and the combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate. After filtration, the solvent is removed under reduced pressure and the residue is purified by flash chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 10:1→5:1). This gives 22.64 g (44.52 mmol, 82% of theory) of a yellowish oil.

Workup

  1. customthe reaction solution is evaporated to dryness
  2. extractionThe aqueous phase is extracted five times with diethyl ether
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent is removed under reduced pressure
  7. customthe residue is purified by flash chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 10:1→5:1)

Sources & evidence

ORD record
ord-2f778b7db8474c98bef58b82be7ceeed
Source dataset
uspto-grants-2011_07
Patent number
US07985876B2

Reaction notes

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