1-Bromopentane → Ethyl 2-oxo-1-pentylcyclopentane-1-carboxylate

HRID 132771Notes

Reaction equation

HRID 132771 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+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CC(C)=O>[CH2:19]([C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 69200134Ethyl 2-oxo-1-pentylcyclopentane-1-carboxylateYield 89.52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under mechanical agitation, 31.20 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 thereto was dropwise added 45.86 ml (purity of 98% of 1-bromo-n-pentane. Upon the completion of the addition, the reaction mixture was heated for reflux for 6 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 36.42 g of colorless liquid as a distillate cut of 156-162° C./22 mmHg was collected. Yield: 89.52%. MS: m/e 227(M+″+1), 226(M+″), 198, 181, 169, 156, 141, 127, 110, 95.

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 6 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 36.42 g of colorless liquid as a distillate cut of 156-162° C./22 mmHg
  11. customwas collected

Sources & evidence

ORD record
ord-0912da9d6d254134b6dc80d8b9cdd37c
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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