Benzyl Bromide → Methyl 1-benzyl-2-oxocyclopentane carboxylate

HRID 132762Notes

Reaction equation

HRID 132762 reaction equation
C(=O)([O-])[O-].[K+].[K+].[O:7]=[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH3:16])=[O:14].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([C:9]1([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:11][CH2:12][C:8]1=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 10847172Methyl 1-benzyl-2-oxocyclopentane carboxylateYield 55.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

29.0 grams of anhydrous potassium carbonate and 132 ml of acetone were mixed, then with stirring, to the resulting mixture was dropwise added a solution of 13.0 ml of methyl 2-oxocyclopentane carboxylate in 66 ml of acetone. After stirring at room temperature for 30 minutes, 13.7 ml of benzyl bromide was dropwise added thereto, and the reaction was allowed to continue under reflux for 6 hours. Then the reaction mixture was cooled to room temperature, filtered, and concentrated, and 150 ml of toluene was added thereto. The resulting solution was washed with water (3×150 ml), dried over anhydrous sodium sulfate, concentrated, and distilled under reduced pressure. 13.4 g of colorless liquid as a distillate cut of 161-162° C./4.8 mmHg was collected. Yield: 55.1%.

Workup

  1. stirringAfter stirring at room temperature for 30 minutes
  2. temperatureunder reflux for 6 hours
  3. filtrationfiltered
  4. concentrationconcentrated
  5. addition150 ml of toluene was added
  6. washThe resulting solution was washed with water (3×150 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. distillationdistilled under reduced pressure
  10. distillation13.4 g of colorless liquid as a distillate cut of 161-162° C./4.8 mmHg was collected

Sources & evidence

ORD record
ord-b93bbbc2655f4f9b84ab2c4ee57aeb80
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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