Ethyl levulinate → 5-(4-Fluoro-phenyl)-4-methyl-pent-4-enoic acid ethyl ester

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Reaction Steps

Sodium ethanolate (0.836 g, 12 mmol) was added under cooling (0° C.) to a solution of 4-fluorobenzyl triphenylphosphonium chloride ([3462-95-1], 5.00 g, 12 mmol) in ethanol, and the mixture was stirred for 45min at r.t. Ethyl levulinate ([539-88-8], 1.77 g, 12 mmol) was added, and the light-orange mixture was refluxed (36 h). After the usual workup, 5-(4-fluoro-phenyl)-4-methyl-pent-4-enoic acid ethyl ester was obtained by column chromatography (silica gel, ethyl acetate/hexane) from the reaction mixture. MS: m/e=237.1 [M+H+].

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