Quinoline → Cis-1-Bromo-tetradec-6-ene

Participants

Reaction Steps

A mixture of alkyne 12 (150 mg, 0.509 mmol), quinoline (0.18 ml, 1.50 mmol) and Lindlar catalyst (Pd, 5% wt % on calcium carbonate, poisoned with lead, 100 mg) was stirred under a H2 atmosphere (balloon pressure) at room temperature for 3 h After removal of the solids residues by filtration through Celite, the filtate was washed with water and extracted with hexanes, dried MgSO4) and concentrated to afford a crude residue which was not purified. The residue was dissolved in dichloromethane at 0° C. and the mixture treated successively with triphenylphosphine (52 mg, 0.20 mmol) and triphenylphosphine dibromide (236 mg, 0.56 mmol) and the resultant mixture stirred for 1 h at 0° C. The mixture was then washed with 10% aq. potassium carbonate, water and dried (MgSO4). Concentration afforded a crude residue which was purified by flash column chromatography (eluent—hexanes) to afford the pure 8 (81%); δH(270 M CDCl3); 0.87 (3H, t, J=6.1 Hz), 1.1-1.65 (14H, m), 1.85 (2H, quin, J 7.0), 2.03 (4H, m), 3.4 (2H, t, J 6.8) and 5.35 (4H, m); δC(67.5 MHz, CDCl3) 27.06, 27.32 27.72, 27.91, 28.04, 28.96, 29.32, 29.37, 29.71, 29.83, 31.96, 32.82, 34.01, 129.31, 130.47.

Provenance & Evidence