1-Octyne → HCID 20147157, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-thiophenecarboxaldehyde (8.5 g, 0.05 mole) was combined with 1-octyne (11.0 g, 0.1 mole) and triethylamine (200 ml). The mixture was degassed under argon and cuprous iodide (950 mg, 10 mole %) and tetrakis (triphenylphosphine) palladium (1.75 g, 5 mole %) were added. The mixture was heated at 105° C. for twenty hours under argon and cooled. The triethylamine was evaporated and the residue purified by chromatography on silica eluting with hexane/chloroform (3:1) to yield the title compound 8.6 g (83.7%) as a yellow oil. mp 130° C., νmax (film) 3320, 2225, 1675, 1050, 805, 780, 675; δ(CDCl3) 0.87(3H, t, J=6 Hz), 1.33(8H, m), 2.33(2H, t, J=6 Hz), 7.13(1H, d, J=6 Hz), 7.65(1H, d, J=6 Hz), 9.87(1H, s).

Provenance & Evidence