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

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Reaction Steps

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).

Provenance & Evidence