Diethyl Malonate → HCID 54423433, compound

HRID 1680657Notes

Reaction equation

HRID 1680657 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].[Na].[CH2:17]([CH:20]([CH2:23]Br)[CH2:21]Br)[CH2:18][CH3:19]>C(O)C>[CH2:10]([O:9][C:1]([C:2]1([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:23][CH:20]([CH2:17][CH2:18][CH3:19])[CH2:21]1)=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxide2×HCID 5360545SodiumHCID 19748706HCID 19748706, compound

Product 1

HCID 54423433HCID 54423433, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Diethyl malonate (96.0 g., 0.608 mol) was added to sodium ethoxide solution [prepared by the addition of 13.8 g. (0.6 gram atom) of sodium to 300 ml. of absolute ethanol] and the mixture was refluxed with stirring. Over a period of one hour, sodium ethoxide solution [prepared by the addition of 12.2 g. (0.5 gram atom) of sodiumto 200 ml. of absolute ethanol] and 2-n-propyl-1,3-dibromopropane (12.2 g., 0.5 mol, prepared as described in Reference Example 1) were added concurrently to the boiling reaction mixture. After the addition was completed, the mixture was refluxed with stirring for 2 hours, and then 400 ml. of ethanol was distilled from the reaction mixture. The residue was mixed with water and extracted with benzene (5×300 ml.). After concentration of the extracts under reduced pressure, a crude product was obtained, which was distilled in vacuo to give the title compound in 84% yield. This compound had the following physical characteristics:

Workup

  1. customprepared by the addition of 13.8 g
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed
  4. stirringwith stirring for 2 hours
  5. distillationof ethanol was distilled from the reaction mixture
  6. additionThe residue was mixed with water
  7. extractionextracted with benzene (5×300 ml.)
  8. customAfter concentration of the extracts under reduced pressure, a crude product was obtained
  9. distillationwhich was distilled in vacuo

Sources & evidence

ORD record
ord-440565a719b2405ebc9f105ff654693d
Source dataset
uspto-grants-1981_06
Patent number
US04275075

Reaction notes

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