Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(4-Fluoro-2-butylamino-phenyl)-acrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of N-methoxy-N-methyl-4-fluoro-2-n-butylamino-benzamide (0.5 g, 1.97 mmol) in THF (8 mL) was added dropwise LiAlH4 (1 M in THF, 1.0 mL) at −45° C. The mixture was stirred for 40 minutes at −35° C. and then quenched by adding saturated aqueous KHSO4 solution. The mixture was diluted with EtOAc, washed with 3 N HCl, and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was reacted with methyl (triphenylphosphoranylidene)acetate (725 mg, 2.17 mmol) in toluene (4 mL) overnight at 100° C. The mixture was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to give the title compound (0.15 g, 30%) after purification by column chromatography (EtOAc:hexane=1:10).

Provenance & Evidence