Diethyl Malonate → 76731-17-4

HRID 1590595Notes

Reaction equation

HRID 1590595 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].[CH:13]1(Br)[CH2:16][CH2:15][CH2:14]1>C(O)C>[CH:13]1([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 78110BromocyclobutaneHCID 5360545Sodium

Product 1

HCID 2163966876731-17-4Yield 42,429.699%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (10.3 g, 0.44 mmol) was dissolved in dry ethanol (300 ml) under a nitrogen atmosphere and to the cooled solution (0° C.) was added diethyl malonate (71 g, 0.44 mmol). After stirring for 15 minutes cyclobutyl bromide (60 g, 0.44 mmol) was added and the solution was heated to reflux overnight. The cooled mixture was evaporated and the residue was partitioned between water and ether. The ether layer was separated, dried over anhydrous magnesium sulphate and evaporated. The residue was distilled to give diethyl cyclobutylmalonate (40 g, 42%) (bp. 74°-75° C. at 0.5 mm Hg).

Workup

  1. additionwas added
  2. temperaturethe solution was heated
  3. temperatureto reflux overnight
  4. customThe cooled mixture was evaporated
  5. customthe residue was partitioned between water and ether
  6. customThe ether layer was separated
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-c7c9e73e96c64f29bfb84560053fa448
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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