1: 76 percent / BuLi / diethyl ether; hexane / 1.) r.t., 2 h, 2.) r.t., 2 h 2: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C 3: 58 percent / AlBr3 / benzene / 3 h / Ambient temperature View Scheme

1.1: nBuLi / diethyl ether; hexane / 0 - 20 °C 1.2: 74 percent / diethyl ether; hexane 2.1: 85 percent / DBU / tetrahydrofuran / 0 - 20 °C 3.1: 93 percent / pyridine / 20 h / 20 °C View Scheme

1.1: nBuLi / diethyl ether; hexane / 0 - 20 °C 1.2: 74 percent / diethyl ether; hexane 2.1: 85 percent / DBU / tetrahydrofuran / 0 - 20 °C View Scheme

1: 1-methoxy-3-tetrahydropyran-2-yloxybenzene With n-butyllithium in diethyl ether; hexane T=0 - 20°C; 2: carbon dioxide in diethyl ether; hexane Further stages.;

1: 76 percent / BuLi / diethyl ether; hexane / 1.) r.t., 2 h, 2.) r.t., 2 h 2: 98 percent / LiCl / dimethylformamide / 6 h / 75 °C View Scheme

1: With n-butyllithium in tetrahydrofuran; hexane T=20°C; 2.75 h; 2: With ethylene dibromide in tetrahydrofuran; hexane T=0 - 20°C; 14 h; 3: With hydrogenchloride in tetrahydrofuran; hexane; water 1 h;

1: 1) butyllithium, 2) 1,2-dibromoethane / 1) hexane, THF, r.t., 3 h, 2) r.t., 1 h 2: dil. HCl / 0.5 h / Ambient temperature 3: 92 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 4: 169 mg / 1) butyllithium, 2) ennecarbonyldiiron / 1) THF, hexane, -100 deg C, 30 min., 2) benzene, reflux, 20 h 5: 94 percent / conc. HCl / tetrahydrofuran / 2 h View Scheme

1.1: nBuLi / cyclohexane; hexane / 0.5 h / Heating 1.2: 52 percent / cyclohexane; hexane / 2 h / Heating 2.1: 98 percent / oxalic acid / methanol; H2O / 1 h / 20 °C View Scheme

1: 1-methoxy-3-tetrahydropyran-2-yloxybenzene With n-butyllithium in tetrahydrofuran; hexane T=20°C; 10 h; 2: With copper(l) iodide T=20°C; 1 h; 3: allyl bromide 2 h; Heating;

1: 1) BuLi / 1) cyclohexane, reflux, 2) Et2O, reflux 2: 5percent aq. oxalic acid / methanol / Ambient temperature View Scheme