Triethylamine → Coumarin, 3-(2-benzoylethyl)-4-hydroxy-

Participants

Reaction Steps

A solution of 0.81 g (5.0 mmol) of 4-hydroxycoumarin, 1.07 g (5.0 mmol) of 2-dimethylaminopropiophenone, and 20 mL of acetonitrile was treated with 0.2 mL (5.0 mmol) of triethylamine and then refluxed for 4 hours. The mixture was cooled to room temperature and poured into 5% sodium hydroxide. The aqueous solution was extracted with ether and acidified to pH 3 with 6N hydrochloric acid. The mixture was extracted with chloroform, and the extract was washed with water, dried, and concentrated to give the title compound, m.p. 149°-151° C. NMR (CDCl3) δ2.99 (m, 2H), 3.52 (m, 2H), 7.26 (m, 2H), 7.48 (m, 3H), 7.60 (m, 1H), 7.94 (dd, 1H), 8.02 (d, 2H), 10.65 (bs, 1H).

Provenance & Evidence