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

HRID 1913790Notes

Reaction equation

HRID 1913790 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][CH:10]([C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:32][CH2:33][C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C:10]([CH2:32][CH2:33][C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)([C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])=[CH:23][CH:24]=1)=[O:4]

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

A solution of 42.61 g (128 mmol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 450 ml of DMF is mixed at room temperature with 62.66 g (192 mmol) of caesium carbonate and 46.75 g (154 mmol) of methyl 4-(2-bromoethyl)benzoate [CAS Reg. No. 136333-97-6]. The mixture is then stirred at room temperature overnight. After conversion is complete, 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 brine and dried over sodium sulphate. After filtration, the solvent is evaporated to dryness in vacuo. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1). 41.35 g (83.6 mmol, 65% of theory) of a colourless solid are obtained.

Workup

  1. customthe reaction solution is evaporated to dryness
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases are then washed with saturated brine
  4. dry with materialdried over sodium sulphate
  5. filtrationAfter filtration
  6. customthe solvent is evaporated to dryness in vacuo
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 13:1)
  8. custom41.35 g (83.6 mmol, 65% of theory) of a colourless solid are obtained

Sources & evidence

ORD record
ord-29b59782745d47b8a651ee345131a550
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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