(nBu)3MgLi in toluene T=-75°C; 0.25 h;

ammonium formate; 10 palladium on active carbon in methanol T=25°C; 0.25 h;

1.1: lithium N,N-diisopropylcarbamate; diisopropylamine; lithium bromide / tetrahydrofuran; hexane / 2 h / -75 °C 1.2: 67 percent / iodine / tetrahydrofuran; hexane / 0.75 h / -75 °C 2.1: 46 percent / piperidine; butyllithium / tetrahydrofuran; hexane / 20 h / -75 °C 3.1: 65 percent / butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 4.1: 87 percent / ammonium formate / palladium (10 percent on charcoal) / methanol / 0.25 h / 25 °C View Scheme

1: 46 percent / piperidine; butyllithium / tetrahydrofuran; hexane / 20 h / -75 °C 2: 65 percent / butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 3: 87 percent / ammonium formate / palladium (10 percent on charcoal) / methanol / 0.25 h / 25 °C View Scheme

1: 65 percent / butyllithium / hexane; tetrahydrofuran / 0.25 h / -75 °C 2: 87 percent / ammonium formate / palladium (10 percent on charcoal) / methanol / 0.25 h / 25 °C View Scheme

potassium permanganate; tetrakis(triphenylphosphine) palladium(0) 1) dioxane, hexane, reflux, 2) H2O, reflux; Yield given. Multistep reaction;

methoxybenzene T=95 - 153°C;

lithium aluminium tetrahydride; chloroformic acid ethyl ester; triethylamine 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min; Yield given. Multistep reaction;

thionyl chloride T=45°C; 18 h;

1: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 2: 52 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme