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

HRID 435949Notes

Reaction equation

HRID 435949 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-4ac532c46b564322a8d72a043c998005
Source dataset
uspto-grants-1977_02
Patent number
US04007171

Reaction notes

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