Hexamethylditin → Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane

Participants

Reaction Steps

A mixture of hexamethylditin (1 g, 3.1 mmol), compound 16 (0.7 g, 2.9 mmol) and tetrakis(triphenylphosphine)palladium (100 mg) in anhydrous THF (20 ml) was heated to reflux under nitrogen for 10 h. After cooling to room temperature, THF was evaporated and methylene chloride (30 mL) was added to the residue. To this mixture, aqueous potassium fluoride (7.0M, 1 mL) was added dropwise with vigorous stirring. The mixture was passed through a Celite bed and the filtrate was washed with brine. The methylene chloride layer was dried (anhydrous Na2SO4), filtered and evaporated in vacuo. The residue was chromatographed using 95:5 hexanes:ethyl acetate to give 62 (0.5 g) in 54% yield; 1H NMR (CDCl3) δ0.32 (9H, s), 6.12 (2H, s), 7.04 (1H, s), 7.82 (1H, s); 13C NMR (CDCl3) δ−6.94, 103.27, 105.82, 114.76, 137.19, 147.90, 149.36, 153.36; HRMS (EI) calcd for C10H13NO4Sn—CH3 m/z: 315.9632; found: 315.9638.

Provenance & Evidence