in tetrahydrofuran T=-78 - -65°C; Inert atmosphere;

ethylene dibromide in tetrahydrofuran room temp.;;

n-butyllithium; diisopropylamine in tetrahydrofuran to a soln. of amine added a soln. of BuLi at 0° C, stirred for 20 min, hydrazone added dropwise, stirred (20 min, 0°C), B comp. added (-78°C), warmed to room temp. for 10 min, qunched at 0°C (sat. aq. NH4Cl) after 4 h; extd. (ethylacetate), dried (MgSO4), solvent removed (vac.), distilled (75°C, 0.5 mm Hg);

1.1: LDA / tetrahydrofuran; hexane / 0.33 h / 0 °C 1.2: tetrahydrofuran; hexane / 4 h / -78 - 20 °C 2.1: 0.44 g / aq. NH4Cl / tetrahydrofuran; hexane View Scheme

multistep reaction: enolate alkylation; other substrates;

potassium in benzene soln. (pinacolato)BCH2I in benzene was added slowly to mixt. K and benzene and heated under reflux overnight; solids were filtered, solvent was removed under vac., products were purified by chromy. on silica (10 percent Et2O/petroleum ether); elem. anal.;

sodium iodide in acetone T=20°C;

in pentane T=20°C; Inert atmosphereSchlenk technique;

1: diiodomethane With boric acid trimethyl ester; methyllithium in tetrahydrofuran; diethyl ether T=-78°C; 1 h; Inert atmosphere; 2: With chloro-trimethyl-silane in tetrahydrofuran; diethyl ether T=-78 - 20°C; 12 h; Inert atmosphere; 3: 2,3-dimethylbutane-2,3-diol in tetrahydrofuran; diethyl ether T=20°C; 72 h; Inert atmosphere;

n-butyllithium in tetrahydrofuran T=20°C;