Ethyl Acetate → 6-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxynaphthalene

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (40 mg) and cuprous bromide (8 mg) were added to a solution of 6,7-dimethoxy-2-naphthalenetriflate (160 mg, 0.48 mmol) and trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane (8, 187 mg, 0.57 mmol) in THF (20 mL). The mixture was stirred at room temperature for 0.5 h., and then refluxed under nitrogen for 18 h. After Cooling, THF was rotaevaporated and ethyl acetate (50 ml) was added to the residue. the solution was washed with water (30 mL). The organic layer was separated and passed through a celite bed to remove suspended particles. The organic layer was then washed with brine, dried (anhydrous Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel using 70:30 hexanes:ethyl acetate to give a mixture of two compounds with same Rf value. The mixture can be separated after the hydrogenation step.

Provenance & Evidence