Diethyl Malonate → diethyl 2-(2-methylallyl)malonate

HRID 1441044Notes

Reaction equation

HRID 1441044 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].[CH2:13](Cl)[C:14](=[CH2:16])[CH3:15]>C(O)C>[CH3:15][C:14](=[CH2:13])[CH2:16][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 112413-Chloro-2-methyl-1-propeneHCID 5360545Sodium

Product 1

HCID 240540diethyl 2-(2-methylallyl)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (5.08 g.) was dissolved in dry ethanol (300 ml.). Diethyl malonate (35 g.) was added and the mixture was stirred for 2 hours. Methallyl chloride (20 g.) was added and the mixture was refluxed with stirring for 4 hours. The mixture was cooled, the solid filtered off and the solvent was removed in vacuo. 2N Hydrochloric acid solution was added and the mixture was extracted with diethyl ether. The ethereal extracts were washed with sodium hydrogen carbonate solution, water and then dried over anhydrous magnesium sulphate. The solvent was removed in vacuo. Distillation gave diethyl 2-methyl-prop-2-enylmalonate as a colourless liquid (28.2 g. b.p. 120°-126° 20 mm.).

Workup

  1. temperaturethe mixture was refluxed
  2. stirringwith stirring for 4 hours
  3. temperatureThe mixture was cooled
  4. filtrationthe solid filtered off
  5. customthe solvent was removed in vacuo
  6. addition2N Hydrochloric acid solution was added
  7. extractionthe mixture was extracted with diethyl ether
  8. washThe ethereal extracts were washed with sodium hydrogen carbonate solution, water
  9. dry with materialdried over anhydrous magnesium sulphate
  10. customThe solvent was removed in vacuo
  11. distillationDistillation

Sources & evidence

ORD record
ord-029450e5c13846d492f035f9607f9740
Source dataset
uspto-grants-1996_03
Patent number
US05502073

Reaction notes

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