Under a nitrogen atmosphere, 14.6 grams (0.36 mole) of sodium hydride (60% in mineral oil) was washed with two 100 mL portions of heptane. The washed sodium hydride was stirred with 350 mL of dimethyl sulfoxide, and the mixture was heated at 50°-55° C. for 3.5 hours until a clear solution formed. The reaction mixture was cooled to 25° C., and a solution of 176.0 grams (0.327 mole) of [3-cyclopropyl-3-(4-trifluoromethoxyphenyl)-2-propen-1-yl]triphenylphosphonium chloride in 300 mL of dimethyl sulfoxide was added in a steady stream. The reaction mixture temperature was maintained at 30° C. or less throughout the addition. Upon completion of addition the reaction mixture was stirred for 30 minutes, and then 69.5 grams (0.323 mole) of 4-fluoro-3-phenoxybenzaldehyde was added in a steady stream during a 15 minute period. The reaction mixture temperature was maintained at 35° during the addition. Upon completion of addition the reaction mixture was stirred for 1 hour and then was poured into a mixture of 2500 mL of aqueous 1N hydrochloric acid in 500 mL of ice. The mixture was stirred until the ice melted and then was extracted with three 1000 mL portions of diethyl ether. The combined extracts were in turn washed with one 1000 mL portion and two 500 mL portions of aqueous 0.5N hydrochloric acid, one 1500 mL portion of an aqueous solution saturated with sodium bicarbonate, two 1000 ml portions of water, and two 500 ml portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 20% methylene chloride in heptane. The appropriate fractions were combined and concentrated under reduced pressure yielding 112.6 grams of 1-cyclopropyl-1-(4-trifluoromethoxyphenyl)-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene.
