1-Cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene → Protrifenbute

Participants

Reaction Steps

Using a Parr hydrogenation apparatus, a solution of 1.7 grams (0.004 mole) of 1-cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl) -1,3-butadiene in 100 mL of absolute ethanol was hydrogenated in the presence of 0.3 gram of Raney nickel (50% in water). Upon completion of the hydrogenation, the reaction mixture was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 10% cyclohexane in hexane. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.2 grams of 1-cyclopropyl-1-(4-chlorophenyl)-4-(4-fluoro-3-phenoxyphenyl)butane. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence