Water → (1-Benzofuran-2-ylethynyl)(trimethyl)silane

Participants

Reaction Steps

A solution of Example 651 (1.00 g, 4.10 mmol), (trimethylsilyl)acetylene (0.80 mL, 5.68 mmol), dichlorobis(triphenylphosphine)palladium(II) (49 mg, 0.13 mmol), diisopropylamine (1.08 mL, 7.74 mmol) and copper iodide (3 mg, 0.258 mmol) in tetrahydrofuran (5 mL) was stirred at room temperature for about 16 h. The solution was poured into water and was extracted with dichloromethane. The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (9:1) as eluent to provide Example 652. 1H NMR (300 MHz, CDCl3) δ 0.29 (m, 9H), 6.94 (s, 1H), 7.23 (m, 1H), 7.33 (m, 1H), 7.43 (m, 1H), 7.54 (d, J=7.8 Hz, 1H).

Provenance & Evidence