反应详情

温度

50 °C

A mixture of 3,3-diethoxy-1-propyne (18.5 g, 0.144 mol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (27.6 g, 0.216 mol) and bis(cyclopentadienyl)zirconium chloride hydride (1.9 g, 0.007 mol) in tetrahydrofuran (75 mL) was heated at 50° C. for 2 days. Triethylamine (2 mL) was added and the solvent was removed in vacuo. The residue was distilled at 90° C. at 10 torr. The residue was purified by column chromatography on neutral alumina using 89:10:1 dichloromethane:ethyl acetate:triethylamine as an eluent. The solvent was removed in vacuo to give the title compound (15.9 g, 53%) as a brown oil. 1H NMR (DMSO-d6, 400 MHz) δ 6.48 (dd, 1H), 5.75 (d, 1H), 4.85 (d, 1H), 3.55–3.67 (m, 2H), 3.40–3.52 (m, 2H), 1.22 (s, 12H), 1.17 (t, 6H).

1. customthe solvent was removed in vacuo
2. distillationThe residue was distilled at 90° C. at 10 torr
3. customThe residue was purified by column chromatography on neutral alumina using 89:10:1 dichloromethane
4. customThe solvent was removed in vacuo