Sodium Carbonate → 7-(5-Oxocyclopent-1-enyl)-5-heptynoic acid methyl ester

HRID 973102Notes

Reaction equation

HRID 973102 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][C:10]1(Cl)[C:15](=[O:16])[CH2:14][CH2:13][CH2:12]C1=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][CH2:6][C:7]#[C:8][CH2:9][C:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH:12]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 544782317-(1-Chloro-2,6-dioxocyclohexyl)-5-heptynoic acid methyl ester

Product 1

HCID 138735017-(5-Oxocyclopent-1-enyl)-5-heptynoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To a solution of 7-(1-chloro-2,6-dioxocyclohexyl)-5-heptynoic acid methyl ester (23.6 g), described in Example 14, in xylene (250 ml) is added powdered sodium carbonate (11.8 g) and the mixture stirred and heated at refluxed for 16 hr. After cooling the mixture is washed with water to neutral, dried over magnesium sulfate, and the solvent evaporated to give the crude cyclopentenone ester. Distillation of the crude ester at 0.6 mm Hg affords 7-(5-oxocyclopent-1-enyl)-5-heptynoic acid methyl ester, b.p. 142° - 156° C.

Workup

  1. temperatureheated
  2. temperatureat refluxed for 16 hr
  3. temperatureAfter cooling the mixture
  4. washis washed with water to neutral,
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated
  7. customto give the crude cyclopentenone ester
  8. distillationDistillation of the crude ester at 0.6 mm Hg

Sources & evidence

ORD record
ord-639d615fb0f84d1395a0c15669f4de22
Source dataset
uspto-grants-1977_10
Patent number
US04054741

Reaction notes

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