1: With diisobutylaluminium hydride; magnesium; lithium chloride in tetrahydrofuran; toluene T=20°C; 1 h; Inert atmosphere; 2: With boric acid trimethyl ester in tetrahydrofuran; toluene T=0°C; Inert atmosphere; 3: With hydrogenchloride; water in tetrahydrofuran; toluene T=0°C; Inert atmosphere;

Li(CH2)3CH3; HCl in tetrahydrofuran (under Ar, Schlenk); soln. of ligand in THF cooled to -90°C, Li(CH2)3CH3 added, stirred for 45 min at -65°C, treated with B(OCH3)3, warmed to room temp., stirred overnight, H2O added, acidified by HCl pH 3-5; extd. with Et2O, organic layer washed with brine, H2O, dried over MgSO4,solvent removed, residue refluxed in H2O for 2 h, filtered, filtrate co oled to 0°C for 10 min, ppt. filtered, washed with pentane, H2O, recrystd. from H2O; elem. anal.;

diethyl ether T=-70°C; und anschliessenden Hydrolyse;

hydrogenchloride; water in tetrahydrofuran T=20°C; 20 h; Inert atmosphere;

1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / |Reflux; |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: water / toluene; tetrahydrofuran; ethanol / 0.75 h / |Inert atmosphere View Scheme

1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene / |Reflux; |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: water / toluene; tetrahydrofuran; ethanol / 0.75 h / |Inert atmosphere View Scheme

1: toluene / 1 h / |Inert atmosphere; |Dean-Stark; |Reflux 2: palladium diacetate; potassium phosphate / tetrahydrofuran / 11 h / 50 °C / |Inert atmosphere 3: hydrogenchloride; water / tetrahydrofuran / 20 h / 20 °C / |Inert atmosphere View Scheme

water byproducts: HOMgBr;

cesium fluoroxysulphate in methanol T=0°C; 10 h;

N,N-dimethyl-N-(4'-methylphenyl)amine N-oxide in dichloromethane T=20°C; 0.0166667 h;