Iodoethane → Ethyl 1-ethyl-2-oxocyclopentane-1-carboxylate

HRID 132765Notes

Reaction equation

HRID 132765 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(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH3:19]>CC(C)=O>[CH2:18]([C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[CH3:19]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 10607544Ethyl 1-ethyl-2-oxocyclopentane-1-carboxylateYield 96.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under vigorously agitation, 31.2 g (purity of 90%,) of ethyl 2-oxocyclopentane carboxylate was added to 76.04 g (purity of 98%) of ground anhydrous potassium carbonate, and after stirring for several minutes, to the mixture was added 100 ml of acetone. The reaction mixture was further stirred for about 15 minutes, then to the mixture was dropwise added 29.51 ml (purity of 98.5%) of ethyl iodide. Upon the completion of the addition, the reaction mixture was heated for reflux for 5 hours. The reaction mixture was filtered under the reduced pressure, and the filter cake was washed with diethyl ether until its color was purely white. Pale yellow filtrate was collected and dried over anhydrous magnesium sulfate, then the solvent was removed. The residue was distilled under reduced pressure, and 32.03 g of colorless liquid as a distillate cut of 130-134° C./18 mmHg was collected. Yield-96.7%. MS: m/e 184(M+′), 156(M+″—C2H5), 140(M+′—OCH2CH3), 139, 101(M+′—CO2CH2CH3), 127(155—CH2CH2), 111(156-OCH2CH3), 55(base).

Workup

  1. stirringThe reaction mixture was further stirred for about 15 minutes
  2. additionUpon the completion of the addition
  3. temperaturethe reaction mixture was heated
  4. temperaturefor reflux for 5 hours
  5. filtrationThe reaction mixture was filtered under the reduced pressure
  6. washthe filter cake was washed with diethyl ether until its color
  7. customPale yellow filtrate was collected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was removed
  10. distillationThe residue was distilled under reduced pressure, and 32.03 g of colorless liquid as a distillate cut of 130-134° C./18 mmHg
  11. customwas collected

Sources & evidence

ORD record
ord-68854d3d137a41be83c56691eb7f58a5
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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