Chloride → HCID 21472389, compound

Participants

Reaction Steps

A mixture of 3-ethynyl-3-hydroxyquinuclidine (750 mg), 4-n-pentyloxyiodobenzene (1.45 g), bis(triphenylphosphine)-palladium. (II) chloride (175 mg), copper (I) iodide (90 mg), triethylamine (5 ml) and dimethylformamide (10 ml) was stirred at 80° C. under an atmosphere of argon for 4 hours. The mixture was cooled, diluted with water (50 ml) and basified with 2M aqueous sodium hydroxide solution (10 ml). The mixture was extracted with ethyl acetate containing 10% methanol (3×30 ml). The organic extracts were combined, and filtered through a short column of silica gel (Varian Bond--elut S1 silica gel). The eluent was evaporated and the residue was crystallised from acetonitrile to give 3-[2-(4-n-pentyloxyphenyl)ethynyl]-3-hydroxyquinuclidine (950 mg) as a solid, m.p. 153°-154° C.; microanalysis, found: C, 76.4; H, 8.9; N, 4.4%; C20H27NO2 requires: C, 76.6; H, 8.68; N, 4.47%; NMR: 0.82-0.95(3H,t), 1.22-1.48(5H,m), 1.6-1.76(3H,m), 1.8-2.0(3H,m), 2.6-2.9(6H,m), 3.9-4.0(2H,t), 5.5(1H,s), 6.85-6.95(2H,d), 7.3-7.4(2H,d); m/z 314(M+H).

Provenance & Evidence