Ethyl Acetate → Prop-2-yn-1-yl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate

Beteiligte Stoffe

Reaktionsschritte

A solution of 200 mmol 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid, 500 mmol propargylic alcohol, 220 mmol 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), and 500 mmol N-ethyldiisopropylamine in 600 mL DMF is stirred at room temperature for 2 h. 1 L of ethyl acetate is added and the solution extracted with 1 L water. The organic layer is separated, dried (Na2SO4), and the solvent evaporated. The crude product is purified via FC (n-hexane/EtOAC 2:1) yielding 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid prop-2-ynyl ester. MS (EI): 374 (18%, M+Na+), 352 (100%, M+H+), 296 (17%). UV (EtOH): λmax=356 nm (ε=31'648).

Herkunft & Nachweise