n-butyllithium in tetrahydrofuran; hexane; ethyl acetate

CH3CH2CH2CH2Li in tetrahydrofuran; hexane (Ar); addn. of 2.5 M soln. of butyllithium in hexanes to THF soln. of manisyl bromide at -78°C, stirring for 20 min at -78°C, addn. of boron compd., stirring overnight at room temp.; quenching with aq. HCl and water, stirring for 6 h at room temp., addn. of diethyl ether, washing with water, separating organic layer, drying over MgSO4, filtration, evapn., NMR and HRMS;

1: With n-butyllithium in tetrahydrofuran; hexanes T=-78°C; 0.833333 h; 2: With hydrogenchloride; water in tetrahydrofuran; hexanes T=0°C;

diethyl ether; magnesium Eintragen des Reaktionsgemisches in festes Kohlendioxid;

C34H43Cl2N3O2Pd in tetrahydrofuran; 1,3-dimethyl-imidazolidin-2-one T=60°C; Negishi cross-coupling; 24 h; Inert atmosphere;

PEPPSITM-IPr in tetrahydrofuran; 1,3-dimethyl-imidazolidin-2-one T=60°C; Negishi cross-coupling; 24 h; Inert atmosphere;

C34H43Cl2N3O2Pd in tetrahydrofuran; 1,3-dimethyl-imidazolidin-2-one T=60°C; Negishi cross-coupling; 24 h; Inert atmosphere;

1.1: 87 percent / N-bromosuccinimide; AIBN / CCl4 / 2 h / Heating 2.1: 93 percent / dimethylformamide / 2 h / 90 °C 3.1: tri-o-tolylphosphane; triethylamine / [Pd(PPh3)2]Cl2 / toluene / 16 h / 165 °C 4.1: Mg / methanol / 6 h / 0 °C 4.2: 96 percent / KOH / methanol; H2O / 24 h / 130 °C 5.1: 98 percent / conc. H2SO4 / 5 h / Heating 6.1: 89 percent / nBuLi; hexamethyldisilazane / tetrahydrofuran; hexane / 0.5 h / -78 °C 7.1: 79 percent / BrCCl3; DBU / CH2Cl2 / 12 h / 20 °C 8.1: 87 percent / NaOH / methanol; H2O / 6 h / Heating View Scheme

1: With tert.-butyl lithium in tetrahydrofuran; DMF (N,N-dimethyl-formamide); pentane T=-78 - 20°C; 3 h; 2: With hydrogenchloride in diethyl ether; water

n-butyllithium in tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) RT, 1 h;