Hydroquinone → HCID 9794667, compound

Participants

Reaction Steps

A mixture of 1.07 g (5 mmol) of N-(5-bromo-pyridin-2-yl)-acetamide, 1.00 g (10 mmol) of butyl vinyl ether, 0.245 g (0.8 mmol) of tri-o-tolylphosphine, 0.090 g (0.4 mmol) of palladium acetate, and 1.10 mL (7.9 mmol) of triethylamine in 10 mL of acetonitrile containing 15 mg of hydroquinone was heated at reflux for about 18 hours. The reaction mixture was then cooled, concentrated, and the residue was taken up in ether and water. The ether phase was separated, washed with water and brine, dried, and concentrated. The residue was chromatographed on silica gel (6:1 benzene--ethyl acetate) to afford 0.254 g of the title product as a colorless oil that rapidly crystallized, mp 55°-58° C. (recrystallization solvent=hexane). 1H nmr (deuteriochloroform): δ=8.48 (m, 1 H); 8.42 (br s, 1 H); 8.24 (m, 1 H); 7.93 (m, 1 H); 4.60 (d, 1 H); 4.23 (d, 1 H); 3.84 (t, 3 H); 2.21 (s, 3 H); 1.77 (m, 2 H); 1.48 (m, 2 H); 0.97 (t, 3 H). ms (El): m/z=234 (M+).

Provenance & Evidence