Triphenylphosphine → HCID 18944187, compound

Participants

Reaction Steps

To a suspension of palladium chloride (11.0 mg, 0.618 mmol) and cuprous iodide (Aldrich gold label, 43.5 mg, 0.229 mmol) in triethylamine (distilled from calcium hydride, 53 mL) was added, sequentially, triphenylphosphine (439 mg, 1.67 mmol), 3-butyn-1-ol (8.0 mL, 106 mmol), and 2-bromobenzaldehyde (10.6 mL, 88.3 mmol). The mixture was refluxed for 7 hours. The mixture was cooled to room temperature, diluted with ether (300 mL) and filtered. The pad was washed with ether (3×50 mL) and the combined filtrates were concentrated in vacuo to an oil: 16.1 g; 1H NMR (270 MHz, deuteriochloroform) δ 10.4 (1H, s), 7.85 (d, J=7 Hz), 7.35-7.50 (m, 3H), 3.0-4.0 (br s, 1H), 3.85 (t, J=6 Hz, 2H), 2.74 (t, J=6 Hz, 2H);

Provenance & Evidence