Ethyl 3-(4-fluorophenyl)pentenoate → Ethyl 3-(4-fluorophenyl)valerate

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Reaction Steps

A mixture of ethyl 3-(4-fluorophenyl)pentenoate (45.65 g, 0.137 mol) and 10% palladium on carbon (0.86 g, Aldrich) in 95% ethanol was shaken under 4 atm hydrogen pressure in a Parr hydrogenator for 1.5 hr. The mixture was filtered and concentrated by spin evaporation in vacuo. Fractional distillation gave 38.95 g (63%) of ethyl 3-(4-fluorophenyl)valerate as a clear oil contaminated with 29% triethyl phosphonoacetate, b.p., 133-142° C. at 17 mm Hg:

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