Dimethyl malonate → Trimethyl cis-3-heptene-1,1,7-tricarboxylate

HRID 372853Notes

Reaction equation

HRID 372853 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[Na].Br[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]>CO.O>[CH:2]([C:1]([O:8][CH3:9])=[O:7])([C:3]([O:5][CH3:6])=[O:4])[CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 3

HCID 7943Dimethyl malonateHCID 5360545SodiumHCID 11253002Methyl cis-7-bromo-5-heptenoate

Product 1

HCID 86734084Trimethyl cis-3-heptene-1,1,7-tricarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dimethyl malonate (39.6 g) is added slowly with cooling and stirring to a solution of 6.9 g of sodium dissolved in 100 ml of absolute methanol and the mixture stirred for 15 min. The bromoester of formula 9, methyl cis-7-bromo-5-heptenoate (65.7 g) is added dropwise. The mixture is heated at reflux for 1 hr., cooled and diluted with water. The mixture is extracted with ether. The ether extracts are dried (Na2SO4) and concentrated. The residue is distilled under reduced pressure to give the title compound, b.p. 140°-150° C/0.7 mm.

Workup

  1. temperaturewith cooling
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 1 hr
  4. temperature, cooled
  5. extractionThe mixture is extracted with ether
  6. dry with materialThe ether extracts are dried (Na2SO4)
  7. concentrationconcentrated
  8. distillationThe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-f4031d35a4a045e894777524efb73023
Source dataset
uspto-grants-1978_05
Patent number
US04092427

Reaction notes

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