1.1: 96 percent / H2SO4; NaN3 / CHCl3 / 45 °C 2.1: NaNO2; HBF4; NaBF4 / tetrahydrofuran / 0 - 20 °C 2.2: 69 percent / chlorobenzene / 3 h / Heating View Scheme

ammonium hydroxide T=150°C;

1.1: thionyl chloride / 2 h / Inert atmosphere; Reflux 2.1: dimethylaluminum chloride / hexane; dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere View Scheme

n-butyllithium 1.) THF, -78 deg C, 30 min, 2a) -78 deg C, 2b) RT, 1 h; Yield given. Multistep reaction;

1: 86 percent / thionyl chloride / methanol / 6 h / Heating 2: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 3: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents 4: 94 percent / hydrochloric acid / aq. ethanol 5: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 6: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme

1: 86 percent / thionyl chloride / methanol / 6 h / Heating 2: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 3: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents View Scheme

copper; xylene

methanol; copper

ueber das Saeurechlorid;

diethyl malonate