3,4-Bis(4-methoxyphenyl)-6-chloropyridazine → HCID 18760037, compound

Participants

Reaction Steps

To a solution of 3,4-bis(4-methoxyphenyl)-6-chloropyridazine 1.2 g (3.7 mmol) in tetrahydrofuran (24 ml), tetrakis(triphenylphosphine)palladium (0.21 g, 0.18 mmol) was added. Under cooling with ice water under an argon gas atmosphere, a 1 M solution (11 ml) of allylmagnesium bromide in diethyl ether was added dropwise. After the resulting mixture was stirred at the same temperature for 1 hour, the temperature of the mixture was allowed to rise to room temperature, followed by further stirring for 2 hours. Water-ethyl acetate was added to the reaction mixture, and the thus-obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. The extract was concentrated under reduced pressure and the residue was left over at room temperature for 3 days. The residue was separated and purified by chromatography on a silica gel column [hexane/ethyl acetate (4/1)], whereby the title compound was obtained as a pale brown oil (0.85 g, 69.8%).

Provenance & Evidence