n-butyllithium 1.) THF, -78 deg C, 80 min, 2.) - 78 deg C to room temp.; Yield given. Multistep reaction;

bis-triphenylphosphine-palladium(II) chloride in tetrahydrofuran Ambient temperature;

tetrakis(triphenylphosphine) palladium(0) in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=60°C; 23 h;

bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide T=60°C; 1 h;

n-butyllithium in diethyl ether; hexane addn. and stirring BuLi in hexane and bromofuran in anhyd. ether at -70°C under N2 (15 min), addn. of tributylchlorostannane, stirring at -70°C (1 h); addn. of satd. aq. NaHCO3, sepn. of the org. phase, washing with satd. aq. NaHCO3 and brine, drying with Na2CO3, evapn., column chromy. (neutral Al2O3, light petroleum), oily compd., elem. anal.;

in neat (no solvent) byproducts: benzonitrile; soln. of acetylene compd. and 4-phenyloxazole is heated at 185°C in a sealed tube for 6-7 d; PhCN is removed under vac., chromy. (alumina, hexane), acetylene compd. is removed by absorbing on alumina overnight, washing (hexane), fractional distn. under vac. (mono-substituted furane), chromy. of the non-volatile residue (alumina, hexane);

tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide T=70°C; 1.5 h;

bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide T=70°C; 2 h;

copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride in N,N-dimethyl-formamide 2 h; Ambient temperature;

sodium methylate; copper(l) iodide; Pd(dibenzylidene acetone)3*CHCl3 in methanol; acetonitrile T=60°C; 2 h;