Cesium carbonate → Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate

HRID 1512203Notes

Reaction equation

HRID 1512203 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.[CH3:20][O:21][C:22]([C:24]1[CH:43]=[CH:42][C:27]([CH2:28][CH:29]([C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])=[CH:26][CH:25]=1)=[O:23]>CN(C=O)C>[CH3:20][O:21][C:22]([C:24]1[CH:25]=[CH:26][C:27]([CH2:28][C:29]([CH2:8][CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)([C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])[C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])=[CH:42][CH:43]=1)=[O:23]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10586287Methyl 4-(2-bromoethyl)benzoateHCID 57831347Diallyl [4-(methoxycarbonyl)benzyl]malonate

Product 1

HCID 59180497Diallyl 2-[4-(methoxycarbonyl)benzyl]-2-{2-[4-(methoxycarbonyl)phenyl]ethyl}malonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At room temperature, 62.66 g (192 mmol) of cesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6] are added to a solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF. 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 water and extracted three times with ethyl acetate. The combined organic phases are then washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness under reduced pressure. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). This gives 41.35 g (83.6 mmol, 65% of theory) of a colorless solid.

Workup

  1. customAt room temperature
  2. customthe reaction solution is evaporated to dryness
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases are then washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent is removed to dryness under reduced pressure

Sources & evidence

ORD record
ord-367fbbecd2ad41d3944480f2d50939b0
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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