Tetrahydrofuran → 3-[3-[[(E)-3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl]amino]phenyl]-(E)-2-propenoic acid methyl ester

Participants

Reaction Steps

(Method G3) A solution of 3-benzo[1,3]dioxol-5-yl-acryloyl chloride (2a) (0.41 g, 1.95 mmol) in tetrahydrofuran (8.0 ml) was added to a mixture of m-aminophenylacrylic acid methyl ester (0.35 g, 1.97 mmol) in tetrahydrofuran (12.0 ml) and NaHCO3 (0.25 g, 3.00 mmol) in water (7.0 ml), and the resultant solution was stirred at room temperature for one hour. The reaction mixture was evaporated and the residue was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water, saturated NaCl, and dried (Na2SO4). The solvent was removed and the residue was chromatographed on silica gel with dichlormethane-methanol (40:1, v/v) as eluent. The obtained product was washed with diethyl ether to give the title compound (0.50 g, 71%). 1H NMR (DMSO-d6, HMDSO), δ: 3.73 (3H, s); 6.09 (2H, s); 6.49 (1H, d, J=16.0 Hz); 6.67 (1H, d, J=16.0 Hz); 6.89-7.83 (8H, m).; 7.98 (1H, br s); 10.23 ppm (1H, br s)

Provenance & Evidence