Tetrahydrofuran → HCID 89544083, compound

Participants

Reaction Steps

87 mg of (3-ethynyl-phenyl)-1-propyne nitrile 63 (0.576 mmol), 120.3 mg of 3-iodobenzaldehyde, and 0.8 ml triethylamine (58.5 mg, 0.576 mmol) were dissolved in 1.5 ml of anhydrous THF, and the solution was deoxygenated by purging argon in it. To this solution was added 22 mg of tetrakistriphenylphosphine palladium (0.019 mmol) then the reaction was allowed to stir for 20 min at room temperature. To this stirring mixture was added 0.9 mg of cuprous iodide (4.5×10−3) then stirred at room temperature for 2 hr, followed by heating further at 50° C. for 2 hr. The solvent was then evaporated in rotatory evaporation to give brown solid. The residue was then purified by silica gel column chromatography using 1:9 dichloromethane:hexane to collect starting material. The polarity was increased to 2:8 dichloromethane:hexane to afford 80 mg of 61 as a golden solid in 55% yield. 1H NMR δ 10.2 (s, 1H), 8.04 (sm, 1H), 7.89 (dm, 1H, J=7.7), 7.78 (m, 2H), 7.69 (dm, 1H, 7.8), 7.60 (dm, 1H, J=7.8), 7.56 (t, 1H, J=7.7), 7.44 (t, 1H, J=7.8); 13C NMR δ 191.30, 137.13, 136.59, 136.27, 134.81, 133.21, 132.90, 129.61, 129.26, 123.99, 123.69, 118.16, 105.22, 89.72, 88.64, 81.77, 63.62; LRMS (GC/MS, CH2Cl2) m/e 255 (M+)

Provenance & Evidence