Butyl bromide → Ethyl 1-n-butyl-2-oxocyclopentane carboxylate

Under vigorously agitation, 52.0 g (purity of 90%) of ethyl 2-oxocyclopentane carboxylate was added to 126.73 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 66.0 ml (purity of 98%,) of 1-bromo-n-butane. 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 53.39 g of colorless liquid as a distillate cut of 140-141° C./16 mmHg was collected. Yield: 83.9%. MS: m/e 212(M+′), 197(M+″—CH3), 184(M+′—CH2CH2), 167(M+′—OCH2CH3), 156(M+′—C4H9,base), 139(M+′—CO2CH2CH3), 127, 111, 55.

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 53.39 g of colorless liquid as a distillate cut of 140-141° C./16 mmHg
11. customwas collected

ORD record

ord-ea3bbbb8870649a2a9aadfe60899fe1e

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07388103B2