5-Iodo-N,N-dimethyl-2-nitrobenzamide → 3-(3-Dimethylcarbamoyl-4-nitrophenyl)propionic acid ethyl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

5-Iodo-N,N-dimethyl-2-nitrobenzamide (2.00 g) was dissolved in tetrahydrofuran (20 mL) and bis(triphenylphosphine)palladium(II) dichloride (0.128 g) was added thereto. After cooling down to 0° C., 0.5M 3-ethoxy-3-oxopropylzinc bromide solution (22.5 mL) was added dropwise thereto, the mixture was stirred at room temperature overnight. The reaction solution was concentrated, dissolved in ethyl acetate (100 mL), washed successively with 1N hydrochloric acid (30 mL) and saturated brine (30 mL), and dried over sodium sulfate. Further, the mixture was purified by column chromatography on silica gel (ethyl acetate:hexane=3:2, v/v) to give the title compound (1.52 g) as a brown oil.

Herkunft & Nachweise