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

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (80 mg) and cuprous bromide (16 mg) were added to a solution of 6,7-dimethoxy-2-naphthalenetriflate (10, 220 mg, 0.655 mmol) and trimethyl(3,4-dimethoxy-6-nitrophenyl)stannane (16, 220 mg, 0.64 mmol) in THF (25 mL). The mixture was stirred at room temperature for 0.5 h., and then refluxed under nitrogen for 32 hr. 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 60:40 hexanes:ethyl acetate to give compound 17; 1H NMR (CDCl3) d 3.95(3H, s), 3.99(6H, s), 4.01(3H, s), 6.86(1H, s), 7.12(1H, s), 7.14(1H, s), 7.23(1H, dd, J=8.4, J=1.8), 7.56(1H, s), 7.61(1H, d, J=1.7), 7.70(1H, d, J=8.4); 13C NMR d 56.4, 56.9, 106.7, 107.0, 108.3, 114.4, 124.9, 125.7, 127.0, 129.0, 129.5, 132.2, 134.6, 141.6, 148.4, 150.4, 152.7.

Provenance & Evidence