Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl ester → 3-Methyl-2-oxocyclopentanecarboxylic acid methyl ester

HRID 58820Notes

Reaction equation

HRID 58820 reaction equation
C[C:2]1([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].[CH3:12][O-].[Na+]>CO>[CH3:12][CH:4]1[CH2:5][CH2:6][CH:2]([C:8]([O:10][CH3:11])=[O:9])[C:3]1=[O:7]

Participants

4

Reactant 2

HCID 121785Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 47381223-Methyl-2-oxocyclopentanecarboxylic acid methyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 1-methyl-2-oxocyclopentanecarboxylate (61.0 g, 0.39 mol) was added dropwise to a freshly prepared solution of NaOMe (0.78 mol) in MeOH (1 L) at ambient temperature. The solution was heated under reflux for 3 h and then concentrated. The residue was dissolved in toluene (1 L) and the resulting solution was heated under reflux for 5 h. The mixture was cooled to ambient temperature, washed with saturated aqueous NaHCO3 (500 mL×3) and brine (300 mL×1), dried over anhydrous sodium sulfate, and concentrated to dryness. The residue was purified by distillation to afford methyl 3-methyl-2-oxocyclopentanecarboxylate (39.0 g, 64% yield).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 3 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in toluene (1 L)
  5. temperaturethe resulting solution was heated
  6. temperatureunder reflux for 5 h
  7. washwashed with saturated aqueous NaHCO3 (500 mL×3) and brine (300 mL×1)
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated to dryness
  10. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-254134018197482cbc6cf27906f27934
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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