Diethyl Malonate → 1,3-Diethyl 2-(1-methylbutyl)propanedioate

HRID 992837

Reaction equation

HRID 992837 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH:14]([CH2:16][CH2:17][CH3:18])[CH3:15]>C(O)C>[CH2:11]([O:10][C:2](=[O:9])[CH:3]([CH:14]([CH3:15])[CH2:16][CH2:17][CH3:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 78902-BromopentaneHCID 5360545Sodium

Product 1

HCID 954491,3-Diethyl 2-(1-methylbutyl)propanedioateYield 67.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (5.24 g, 0.23 g atm) was reacted with 25 mL of absolute ethanol. To this solution was added dropwise, with stirring, diethyl malonate (36.0 mL, 0.24 mol). The solution was heated to reflux and 2-bromopentane (29.0 mL, 0.23 mol) was added dropwise. After refluxing overnight, the reaction was cooled and the ethanol removed on a rotovap. The product was washed with water, dried with MgSO4 and fractionally distilled to give 35.7 g of the desired product.

Workup

  1. additionTo this solution was added dropwise
  2. temperatureThe solution was heated
  3. temperatureto reflux
  4. temperatureAfter refluxing overnight
  5. temperaturethe reaction was cooled
  6. customthe ethanol removed on a rotovap
  7. washThe product was washed with water
  8. dry with materialdried with MgSO4
  9. distillationfractionally distilled

Sources & evidence

ORD record
ord-c161b0f5c00a47508e39a5ff3958dd94
Source dataset
uspto-grants-2002_10
Patent number
US06472227B1

Linked notes

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