Benzene, 1,3-diethynyl- → Methyl 3-(4-((3-ethynylphenyl)ethynyl)phenyl)propanoate

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The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (120 mg, 0.41 mmol) and 1,3-diethynylbenzene (0.06 mL, 0.45 mmol) according to the general procedure IC, with the exception that the reaction was performed at room temperature, to give 52 mg (43%) of an yellow-brown gummy oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:3). Rf: 0.41 (EtOAc:hexanes, 1:2); 1HNMR (CDCl3) δ 7.65 (s, 1H), 7.49-7.42 (m, 4H), 6.31-7.29 (m, 1H), 7.19-7.17 (m, 2H), 3.67 (s, 3H), 3.09 (s, 1H), 2.99-2.93 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 141.1, 135.0, 131.8, 131.7, 128.4, 123.7, 122.4, 120.8, 90.0, 88.0, 82.8, 77.7, 51.6, 35.3, 30.8; EI-MS m/z 288 (M+).

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