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

HRID 132771Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132771
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 69200134Ethyl 2-oxo-1-pentylcyclopentane-1-carboxylateAusbeute 89,52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0912da9d6d254134b6dc80d8b9cdd37c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388103B2

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