Allyl bromide → 1-Allyl-5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester

HRID 866567Notes

Reaction equation

HRID 866567 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH:9]([CH2:10][C:11]#[N:12])[CH2:8][CH2:7][C:6]1=[O:13])=[O:4].[CH2:14](Br)[CH:15]=[CH2:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1([CH2:16][CH:15]=[CH2:14])[CH:9]([CH2:10][C:11]#[N:12])[CH2:8][CH2:7][C:6]1=[O:13])=[O:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 24977136Methyl 2-(cyanomethyl)-5-oxocyclopentane-1-carboxylate

Product 1

HCID 541973371-Allyl-5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl esterYield 69.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester (100 mg, 0.58 mmol) and allyl bromide (121 mg, 1 mmol) were dissolved in acetone (5ml). Potassium carbonate (138 mg, 1 mmol) was added to the solution. The mixture was heated under refluxing with stirring for 5 hours and then was cooled and was filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by a silica gel column chromatography (ethyl acetate: n-hexane=1: 4) to obtain 89 mg of 1-allyl-5-cyanomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester as viscous oily product. Yield: 69%. Infrared spectrum(cm-1): 2235, 1755, 1730, 1640, 925. NMR spectrum (CDCl3) δ : 1.60 - 3.05 (m, 9H), 3.73 (s, 3H), 4.88 - 6.07 (m, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing
  3. temperaturewas cooled
  4. filtrationwas filtered
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (ethyl acetate: n-hexane=1: 4)

Sources & evidence

ORD record
ord-d56418ef44ff4b67bb2e6832539c132a
Source dataset
uspto-grants-1978_07
Patent number
US04100184

Reaction notes

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