Diethyl Malonate → Diethyl isobutylmalonate

HRID 1415388Notes

Reaction equation

HRID 1415388 reaction equation
[Na].[CH2:2]([O:4][C:5](=[O:12])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3].[CH2:13](I)[CH:14]([CH3:16])[CH3:15]>>[CH2:2]([O:4][C:5](=[O:12])[CH:6]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:3]

Participants

4

Reactant 3

HCID 7761Diethyl MalonateHCID 10556Isobutyl iodideHCID 5360545Sodium

Product 1

HCID 25047Diethyl isobutylmalonate

Procedure

A solution of 23 g of sodium in 1500 ml of anhydrous alcohol was treated, with stirring, with 160.16 g of malonic acid diethyl ester. After stirring for 30 minutes, 184.03 g of isobutyl iodide were added dropwise to the solution. The mixture was then stirred for and additional further 15 hours at 20° and subsequently evaporated under reduced pressure. The residue was stirred with diethyl ether, filtered off from the solid material and evaporated under reduced pressure. The brown oil remaining as the residue was fractionated twice in a high vacuum. There was obtained 45.8 g of a main fraction of isobutylmalonic acid diethyl ester, boiling point 64°/0.6 mm Hg.

Workup

  1. stirringThe mixture was then stirred for and additional further 15 hours at 20°
  2. customsubsequently evaporated under reduced pressure
  3. stirringThe residue was stirred with diethyl ether
  4. filtrationfiltered off from the solid material
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a35d382146ea4239b400fa8de5902f3f
Source dataset
uspto-grants-1977_01
Patent number
US04005073

Reaction notes

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