2-Benzofurancarboxylic acid ethyl ester

The Uses of 2-Benzofurancarboxylic acid ethyl ester

Ethyl Coumarilate has been used as a reactant for the preparation of benzofuropyridines that have a high affinity for the α2-adrenoceptor.

Preparation

Synthesis of ethyl benzofuran-2-carboxylate: Salicylaldehyde (20.0 mL, 0.164 mol) and diethyl bromomalonate (40.0 mL, 0.168 mol) in ethyl methyl ketone (40.0 mL, 0.555 mol) was treated with anhydrous potassium carbonate (20.0 g,0.869 mol). The reaction mixture was refluxed for 18 h on steam bath. Ethyl methyl ketone was distilled off under reduced pressure and the residue formed was dissolved in 400 mL of water and cooled in an ice-bath. It was acidified with dil H2SO4. The product formed was extracted with 25 mL portion of solvent ether twice and the extract was washed with sodium bicarbonate solution. It was dried over calcium chloride. Solvent was removed and the residue ethyl benzofuran-2-carboxylate was dried.

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 6315, 1986 DOI: 10.1016/S0040-4039(00)87796-5