ethyl (2Z)-3-iodoprop-2-enoate → 5-Thiophen-2-yl-pent-2-en-4-ynoic acid ethyl ester

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The general procedure was used to convert 2-Ethynyl-thiophene and (Z)-ethyl-3-iodoacrylate to the title product. Purification by flash chromatography (10% ethyl acetate in hexane as the eluent) gave the analytically pure product as a light yellow oil (230 mg, 62% yield). 1H NMR (400 MHz, CDCl3) δ 7.36-7.35 (dd, J=5.1, 1.0, 1H), 7.33-7.32 (dd, J=3.6, 1.0, 1H), 7.02-7.00 (m, 1H), 6.36-6.33 (d, J=11.4, 1H), 6.10-6.08 (d, J=11.4, 1H), 4.29-4.23 (q, J=7.1, 2H), 1.36-1.32 (t, J=7.1, 3H). 13C NMR (100 MHz, CDCl3) δ 164.79, 133.49, 129.19, 127.62, 127.36, 122.57, 122.29, 94.50, 90.82, 60.51, 14.31. Anal. Calcd. for C11H10O2S: C, 64.05; H, 4.89; S, 15.55; Found C, 64.01; H, 4.95; S, 15.27.

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