1-Butoxy-4-iodobenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (+) 3-ethynyl-3-hydroxyquinuclidine (180 mg), 4-butoxyiodobenzene (330 mg), bis(triphenylphosphine)-palladium (II) chloride (42 mg),copper (I) iodide (21 mg), triethylamine (2.5 ml) and dimethylformamide (5 ml) was stirred under argon at ambient temperature for 4 hours. The triethylamine and dimethylformamide were removed by evaporation. A solution of 2M sodium hydroxide (10 ml) was added and the mixture extracted with dichloromethane (3×10 ml). The combined organic extracts were washed with water (10 ml), dried (MgSO4) and evaporated to a gum. This gum was further purified by flash column chromatography on silica gel using a mixture of 5% methanol in dichloromethane containing 1% ammonia (density, 0.88 g(cm3) as eluent, followed by crystallisation from ethyl acetate to give (+)-3-[2-(4-butoxyphenyl)ethynyl)-3-hydroxyquinuclidine (120 mg) as a solid, m.p. 115°-116° C.; microanalysis, found C, 75.4; H, 8.4; N, 4.5%; C19H25NO2 0.2H2O requires: C,75.35; H, 8.39, N, 4.63%; NMR: 0.86-0.99(3H,t), 1.2-1.5(3H,m), 1.5-1.71(3H,m), 1.72-1.97(3H,m), 2.6-2.72(4H,m), 2.75-2.85(1H,d), 3.0-3.1(1H,d), 3.9-4.01(2H,t), 5.15(1H,s), 6.85-6.95(2H,d), 7.27-7.37(2H,d); m/z 300(M+H) α=[+26.6]58921 (c=1; methanol). The triethylamine and dimethylformamide were removed by evaporation A solution of 2M sodium hydroxide (10 ml) was added the mixture extracted with dichloromethane (3×10 ml) The combined organic extracts were washed with water (10 ml) dried (MgSO4) evaporated to a gum This gum was further purified by flash column chromatography on silica gel using a mixture of 5% methanol in dichloromethane containing 1% ammonia (density, 0.88 g(cm3) as eluent followed by crystallisation from ethyl acetate