Methyl iodide → Ethyl 1-methyl-2-oxocyclopentane-1-carboxylate

HRID 58823

Reaction equation

HRID 58823 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:12]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:12][C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 227353Ethyl 1-methyl-2-oxocyclopentane-1-carboxylateYield 92.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of ethyl 2-oxocyclopentanecarboxylate (20.3 g, 0.130 mol) and K2CO3 (53.8 g, 0.390 mol) in acetone (90 mL) was added MeI (36.9 g, 0.250 mol) at ambient temperature. The reaction mixture was stirred for 30 min at ambient temperature and then heated under reflux for 1 h. Acetone was removed under reduced pressure and diethyl ether (200 mL) was added to the residue. The resulting mixture was stirred for 15 min and filtered. The filtrate was concentrated under reduced pressure followed by distillation under vacuum to afford ethyl 1-methyl-2-oxocyclopentanecarboxylate (20.5 g, 92% yield).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 h
  3. customAcetone was removed under reduced pressure and diethyl ether (200 mL)
  4. additionwas added to the residue
  5. stirringThe resulting mixture was stirred for 15 min
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. distillationfollowed by distillation under vacuum

Sources & evidence

ORD record
ord-a983ff367a9f4ab487ef0b59ea207ddd
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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