反应详情

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 2.5M 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 2N hydrochloric acid. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water, 2N 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. temperatureis cooled to -55° to -60° C.
2. temperaturewarmed to and
3. temperaturecooled to -55° to -60° C.
4. temperaturewarmed to and
5. stirringstirred at room temperature overnight
6. customquenched with ethyl acetate and 2N hydrochloric acid
7. extractionThe resultant aqueous mixture is extracted with ethyl acetate
8. washwashed sequentially with water, 2N hydrochloric acid and water
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated in vacuo
11. customto obtain a residue