Benzyl Bromide → Benzyl cyclopent-3-enecarboxylate

HRID 58873Notes

Reaction equation

HRID 58873 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH:7]1([C:12]([OH:14])=[O:13])[CH2:11][CH:10]=[CH:9][CH2:8]1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH:7]1([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:11][CH:10]=[CH:9][CH2:8]1

Participants

5

Reactant 3

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

Product 1

HCID 22084261Benzyl cyclopent-3-enecarboxylateYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

K2CO3 (35.0 g, 255 mmol) was added to a solution of cyclopent-3-enecarboxylic acid (20.0 g, 178 mmol) in acetonitrile (500 mL) followed by addition of benzyl bromide (36.6 g, 214 mmol). The reaction mixture was stirred for 12 h at ambient temperature. The mixture was filtered and washed with acetonitrile (200 mL). The filtrate and washings were combined and concentrated to dryness. The residue was purified by flash column chromatography on silica gel (hexane/EtOAc=10:1) to afford benzyl cyclopent-3-enecarboxylate (26.5 g, 74% yield) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with acetonitrile (200 mL)
  3. concentrationconcentrated to dryness
  4. customThe residue was purified by flash column chromatography on silica gel (hexane/EtOAc=10:1)

Sources & evidence

ORD record
ord-34cebf29e9254682a414ec0d9d3bf15b
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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