Diethyl Malonate → Diethyl allylmalonate

HRID 82246

Reaction equation

HRID 82246 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[O-]CC.[Na+].Br[CH2:17][CH:18]=[CH2:19]>C(O)C>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([CH2:19][CH:18]=[CH2:17])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 7841Allyl bromideHCID 2723922Sodium ethoxide

Product 1

HCID 74900Diethyl allylmalonateYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Malonic acid diethyl ester (100 g, 0.625 mol) was added dropwise at 0° C. to a mixture of sodium ethoxide (46.8 g, 0.688 mol) in ethanol (1 L). The reaction mixture was stirred for 4 hours. 3-Bromo-propene (83.2 g, 0.688 moles) was added dropwise to the mixture at 0° C. After addition, the mixture was warmed to reflux and stirred overnight. The mixture was cooled to room temperature, filtered and the solvent was removed in vacuo to afford the title compound in 86% yield, 100 g which was used for the next step without further purification.

Workup

  1. additionAfter addition
  2. temperaturethe mixture was warmed
  3. temperatureto reflux
  4. stirringstirred overnight
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d4a4ffdcc3124934a6161152b96968f9
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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