Potassium Carbonate → (E)-methyl 2-[2-(4-chloro-1,3,5-triazin-2-yloxy)phenyl]-3-methoxypropenoate

Participants

Reaction Steps

To a stirred solution of 2,6-dichloro-1,3,5-triazine (0.3g, 2 mmol; made according to R L N Harris, Synthesis, 1981, 907) and potassium carbonate (0.28g, 2 mmol) in dry acetonitrile (25 ml) at 0° C. under an atmosphere of nitrogen was added dropwise a solution of (E)-methyl 2-(2-hydroxyphenyl)-3-methoxypropenoate (0.42g, 2mmol) in dry acetonitrile (7 ml). Anhydrous caesium fluoride (0.30g, 2 mmol) and a catalytic amount of 18-crown-6 were added with stirring and the temperature was allowed to rise to room temperature. After stirring overnight, the reaction mixture was filtered and evaporated to leave a yellow/orange paste. Chromatography (eluent diethyl ether) afforded (E)-methyl 2-[2-(4-chloro-1,3,5-triazin-2-yloxy)phenyl]-3-methoxypropenoate (0.42white solid, m.p. 137°-140° C.; Infrared max. 1704, 1631 cm-1 ; 1H NMR (CDCl3) δ63.63(3H,s); 3.75(3H,s); 7.19-7.29(lH,m); 7.31-7.45(3H,m); 7.47(lH,s); 8.74(lH,s) ppm.

Provenance & Evidence