methyllithium in diethyl ether

methyllithium; methyl iodide in tetrahydrofuran; diethyl ether at -20°C addn. of MeLi in Et2O to Bu3SnLi in THF, addn. of this mixt. to a suspn. of CuCN in THF, stirring for 15 min, cooling to -78°C, addn. of acetylene, after 30 min addn. of electrophile, after 15 to 30 min. warming to 0°C; after 1 h quenching of mixt. with NH4Cl;

in tetrahydrofuran; hexane a soln. of stannyllithium in THF and MeLi in hexane and CuCN is stirred at -78°C for 30 min, dropwise addn. of acetylene and MeI in THF, the mixt. is stirred at this temp. for 1 h and then at 0°C for 3 h (under nitrogen); saturated aq. NH4Cl is added, extn. with Et2O, drying (MgSO4) and chromy., elem. anal.;

palladium diacetate; [14C]-Orotic acid; cesium fluoride in 1,4-dioxane T=100°C; Stille Cross Coupling; 18 h; Sealed tubeInert atmosphereSchlenk technique;

tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane; lithium chloride in N,N-dimethyl-formamide T=120 - 130°C; Yield given;

dichloro bis(acetonitrile) palladium(II) in N,N-dimethyl-formamide T=20°C; Stille coupling; 7 h;