Methyl iodide → Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl ester

HRID 58819Notes

Reaction equation

HRID 58819 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH3:10])=[O:8].[C:11]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:11][C:3]1([C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 121785Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl esterYield 82.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 2-oxocyclopentanecarboxylate (67 g, 0.47 mol), K2CO3 (163 g, 1.18 mol) and MeI (167 g, 1.18 mol) in acetone (500 mL) was heated under reflux for 12 h. The mixture was cooled to ambient temperature and then concentrated. The residue was dissolved in EtOAc (800 mL) and the resulting solution was 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 1-methyl-2-oxocyclopentanecarboxylate (60.5 g, 82% yield).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 h
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc (800 mL)
  5. washthe resulting solution was washed with saturated aqueous NaHCO3 (500 mL×3) and brine (300 mL×1)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-0febed90a60a4aaaafe14ab0cfc40b9f
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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