反应详情

温度

-57.5 °C

A mixture of (4-fluoro-3-phenoxybenzyl)triphenyl phosphonium bromide (41.77 g, 0.077 mol) in tetrahydrofuran is cooled to −55 to −60° C., treated dropwise with a 2.5 M solution of butyllithium in hexanes (32.15 mL, 0.080 mol), warmed to and stirred at room temperature for 2 hours, cooled to −55 to −60° C., treated dropwise with a solution of 2-fluoro-3-cyclopropyl-3-(p-chlorophenyl)acrylaldehyde (15.7 g, 0.070 mol) in tetrahydrofuran, warmed to and stirred at room temperature overnight, and quenched with ethyl acetate and 2 N hydrochloric acid. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 2 N hydrochloric acid and water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and an ethyl acetate/hexanes solution (1:9) gives the title product as an oil (26.0 g, 91%).

1. temperaturewarmed to and
2. temperaturecooled to −55 to −60° C.
3. temperaturewarmed to and
4. stirringstirred at room temperature overnight
5. customquenched with ethyl acetate and 2 N hydrochloric acid
6. extractionThe resultant aqueous mixture is extracted with ethyl acetate
7. washwashed sequentially with water, 2 N hydrochloric acid and water
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated in vacuo
10. customto obtain a residue