Benzyl Bromide → HCID 561517, compound

HRID 2384078Notes

Reaction equation

HRID 2384078 reaction equation
[CH:1]1([C:6]([OH:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([O:7][C:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 18840Cyclopentanecarboxylic acid

Product 1

HCID 561517HCID 561517, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of cyclopentanecarboxylic acid (1.14 g, 10 mmol) in DMF (15 mL) is added K2CO3 (2.07 g, 15 mmol) and benzyl bromide (1.71 g, 10 mmol). The suspension is stirred at room temperature for 18 hours. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over MgSO4 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (heptane:EtOAc, 10:1) to give cyclopentanecarboxylic acid benzyl ester.

Workup

  1. customThe mixture is quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer is washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent is removed under reduced pressure
  7. customthe residue is purified by flash chromatography (heptane:EtOAc, 10:1)

Sources & evidence

ORD record
ord-8dcb0a6838544385842124d41f334c75
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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