Diethyl Malonate → Diethyl Decylmalonate

HRID 993082Notes

Reaction equation

HRID 993082 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](Br)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(O)C>[CH2:13]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 81731-BromodecaneHCID 5360545Sodium

Product 1

HCID 252345Diethyl Decylmalonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of sodium (0.46 g) in 10 of anhydrous ethanol is added with 3.35 ml of diethyl malonate in 3 ml of ethanol and successively with a solution of decylbromide (4.15 ml) in 3 ml of ethanol. The reaction mixture is refluxed for 4 hours, then the precipitate is filtered off and the filtrate is concentrated to dryness. The residue is redissolved in a saturated aqueous solution of sodium hydrogensulfate and it is extracted with ethyl acetate. The organic extract is dried over sodium sulfate and the solvent is evaporated off. The resulting residue is used as such in the successive reaction.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. filtrationthe precipitate is filtered off
  3. concentrationthe filtrate is concentrated to dryness
  4. dissolutionThe residue is redissolved in a saturated aqueous solution of sodium hydrogensulfate and it
  5. extractionis extracted with ethyl acetate
  6. extractionThe organic extract
  7. dry with materialis dried over sodium sulfate
  8. customthe solvent is evaporated off
  9. customsuch in the successive reaction

Sources & evidence

ORD record
ord-d36253a925204fbb94f22938a870a9e0
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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