Water → Benzyl 3-oxocyclopentanecarboxylate

HRID 1160607Notes

Reaction equation

HRID 1160607 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5]1)([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[O:9]=[C:6]1[CH2:7][CH2:8][CH:4]([C:1]([O:3][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:2])[CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2277983-Oxocyclopentanecarboxylic acid

Product 1

HCID 14530748Benzyl 3-oxocyclopentanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-carboxycyclopentanone (640 mg, 5.0 mmol) in 8 mL of degassed DMF was added potassium carbonate (828 mg, 5.99 mmol) and benzyl bromide (0.65 mL, 5.49 mmol). After 4 hours at room temperature, the reaction mixture was poured into 50 mL of water and extracted 3 times with EtOAc. The combined organic layers were washed with water and dried over sodium sulfate. Filtration and solvent removal provided material that was subjected to silica gel chromatography eluting with 10% EtOAc in hexanes to yield benzyl 3-oxocyclopentanecarboxylate.

Workup

  1. extractionextracted 3 times with EtOAc
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and solvent removal
  5. customprovided material that
  6. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-850faf859de6495bbc7ecf00d17421a9
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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