Tetrahydrofuran → 6-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxy-5-nitronaphthalene

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium (0) (100 mg) and cuprous bromide (20 mg) was added to a solution of 7-Methoxy-1-nitro-2-trifluoromethanesulfonyloxy-naphthalene 53 (366 mg, 1.04 mmol) and trimethylnitroarylstannane 62 (500 mg, 1.52 mmol) in THF (30 mL) at room temperature and stirred for 0.5 h. The mixture was then refluxed under N2 overnight. After cooling, THF was evaporated and ethyl acetate (30 mL) was added to the residue. The solution was washed with water. 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 evaporated in vacuo. The residue was chromatographed using a 70:30 mixture of hexanes:ethyl acetate to give 54 (160 mg) in 42% yield; mp 187-189° C.; IR (KBr) 2925, 1628, 1526, 1487, 1364, 1332, 1265, 1230 cm−1; 1H NMR (CDCl3) δ3.92 (3H, s), 6.19 (2H, d), 6.76 (1H, s), 7.12 (1H, d, J=2.5), 7.18 (1H, d, J=8.3), 7.28 (1H, dd, J1=9.0, J2=2.3), 7.70 (1H, s), 7.85 (1H, d, J=9.2), 7.93 (1H, d, J=8.4), 13C NMR δ56.08, 100.59, 103.93, 106.31, 110.70, 121.54, 124.07, 126.47, 128.71, 129.55, 130.33, 130.99, 131.23, 142.83, 148.92, 152.07, 160.68.

Provenance & Evidence