pyridine; Dess-Martin periodane in dichloromethane T=0 - 20°C; 1 h;

1: 83 percent / sodium hydride / diethyl ether / 5 h reflux, overnight at room t. 2: stannic chloride / CH2Cl2 / Ambient temperature 3: 100 percent / sodium borohydride / ethanol; H2O / 4 h / Ambient temperature 4: 58 percent / POCl3 / pyridine / 22 h / 95 °C 5: 0.53 g / LiAlH4 / diethyl ether / from -40 to 0 degC over 1 h 6: MnO2 / hexane / 16 h / Ambient temperature View Scheme

1: stannic chloride / CH2Cl2 / Ambient temperature 2: 100 percent / sodium borohydride / ethanol; H2O / 4 h / Ambient temperature 3: 58 percent / POCl3 / pyridine / 22 h / 95 °C 4: 0.53 g / LiAlH4 / diethyl ether / from -40 to 0 degC over 1 h 5: MnO2 / hexane / 16 h / Ambient temperature View Scheme

1: 100 percent / sodium borohydride / ethanol; H2O / 4 h / Ambient temperature 2: 58 percent / POCl3 / pyridine / 22 h / 95 °C 3: 0.53 g / LiAlH4 / diethyl ether / from -40 to 0 degC over 1 h 4: MnO2 / hexane / 16 h / Ambient temperature View Scheme

1: 58 percent / POCl3 / pyridine / 22 h / 95 °C 2: 0.53 g / LiAlH4 / diethyl ether / from -40 to 0 degC over 1 h 3: MnO2 / hexane / 16 h / Ambient temperature View Scheme

1: 0.53 g / LiAlH4 / diethyl ether / from -40 to 0 degC over 1 h 2: MnO2 / hexane / 16 h / Ambient temperature View Scheme

aluminum isopropoxide P=12 Torr; anschl. mit 4-Methoxy-benzaldehyd;

1: sodium tetrahydroborate / methanol / -78 - -30 °C 2: thionyl chloride; pyridine / dichloromethane / 5 h / 0 - 20 °C 3: diisobutylaluminium hydride / dichloromethane; hexane / 1.5 h / -78 - 0 °C 4: Dess-Martin periodane; pyridine / dichloromethane / 1 h / 0 - 20 °C View Scheme

1: diisobutylaluminium hydride / dichloromethane; hexane / 1.5 h / -78 - 0 °C 2: Dess-Martin periodane; pyridine / dichloromethane / 1 h / 0 - 20 °C View Scheme

1: 80 percent / conc. HCl / 0.02 h / Heating 2: 1.) TMEDA, n-BuLi / 1.) hexanes, a.) -78 deg C, 60 min b.) RT, 1.5h; 2.) RT 3h. View Scheme