1-Ethynyl-4-nitrobenzene → 5-(4-Nitro-phenyl)-pent-2-en-4-ynoic acid ethyl ester

Participants

Reaction Steps

The general procedure was used to convert 1-Ethynyl-4-nitro-benzene and (Z)-ethyl-3-iodoacrylate to the title product except using 1.6 mmol of acetylene and 1.8 mmol vinyl iodide. Purification by flash chromatography (20% ethyl acetate in hexane as the eluent) gave the analytically pure product as a yellow solid (350 mg, 89% yield). 1H NMR (400 MHz, CDCl3) δ 8.22-8.19 (d, J=8.9, 2H), 7.68-7.65 (d, J=8.9, 2H), 6.38-6.35 (d, J=11.4, 1H), 6.26-6.23 (d, J=11.4, 1H), 4.29-4.24 (q, J=7.1, 2H), 1.35-1.31 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 164.38, 147.48, 132.66, 130.32, 129.41, 123.57, 121.67, 97.99, 90.64, 60.64, 14.23. Anal. Calcd. for C13H11NO4: C, 63.67; H, 4.52; N, 5.71; Found C, 63.45; H, 4.44; N, 5.65. m.p.: 76.0°-78.0° C.

Provenance & Evidence