Ethyl propiolate → HCID 90460390, compound

Participants

Reaction Steps

A solution of 4-azidobenzonitrile (5.3 g, 36.77 mmol, 1.00 equiv) and ethyl prop-2-ynoate (10.82 g, 110.30 mmol, 3.00 equiv) in ethanol (160 mL) was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 650 mg (7%) of ethyl 1-(4-cyanophenyl)-1H-1,2,3-triazole-5-carboxylate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.54 (s, 1H), 8.11 (d, J=8.0 Hz, 2H), 7.90 (d, J=8.0 Hz, 2H), 4.27-4.22 (m, 2H), 1.20 (t, J=6.8 Hz, 3H) ppm. LCMS (method C, ESI): RT=0.87 min, m/z=243.1 [M+H]+ and 2.4 g (26%) of ethyl 1-(4-cyanophenyl)-1H-1,2,3-triazole-4-carboxylate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.66 (s, 1H), 8.24 (d, J=8.8 Hz, 2H), 8.13 (d, J=8.8 Hz, 2H), 4.41-4.36 (m, 2H), 1.36 (t, J=7.2 Hz, 3H) ppm. LCMS (method D, ESI): RT=1.71 min, m/z=243.1 [M+H]+.

Provenance & Evidence