Water → Benzyl cyclopent-3-enecarboxylate

HRID 1160610Notes

Reaction equation

HRID 1160610 reaction equation
[CH:1]1([C:6]([OH:8])=[O:7])[CH2:5][CH:4]=[CH: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.O>CN(C=O)C>[CH:1]1([C:6]([O:8][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 8537563-Cyclopentene-1-carboxylic acid

Product 1

HCID 22084261Benzyl cyclopent-3-enecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclopent-3-ene-1-carboxylic acid (9.63 g, 85.88 mmol) in 143 mL of degassed DMF was added potassium carbonate (14.24 g, 103.06 mmol) and benzyl bromide (11.24 mL, 94.47 mmol). The mixture was stirred for 2 hours at ambient temperature, and then poured into 150 mL of water and extracted with ethyl acetate. The extracts were washed with water and brine, and dried over sodium sulfate. Filtration and concentration under vacuum afforded benzyl cyclopent-3-ene-1-carboxylate as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration under vacuum

Sources & evidence

ORD record
ord-09f56737dd3041d6a74d443ffc1aa67d
Source dataset
uspto-grants-2010_10
Patent number
US07816380B2

Reaction notes

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