AlCl3, aluminium chloride in 1,4-dioxane T=20°C; 15 h; Heating / reflux;

hydrogen; palladium on activated charcoal in ethanol P=760 Torr; 3 h; Ambient temperature;

aluminium trichloride in dichloromethane Ambient temperature;

1: 67 percent / pyridine / tetrahydrofuran / 1.) room temperature, 40 min, 2.) reflux, 1 h 2: 91 percent / 0.17 h / 140 - 150 °C 3: 70 percent / sodium borohydride / 1 h / Heating 4: 80 percent / aluminium chloride / nitrobenzene / 6 h / 50 - 60 °C View Scheme

1: 1.) LDA / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) -78 deg C-room temperature, 4 h 2: 81 percent / water / 16 h 3: 91 percent / acetyl chloride / 0.5 h / Heating 4: 67 percent / pyridine / tetrahydrofuran / 1.) room temperature, 40 min, 2.) reflux, 1 h 5: 91 percent / 0.17 h / 140 - 150 °C 6: 70 percent / sodium borohydride / 1 h / Heating 7: 80 percent / aluminium chloride / nitrobenzene / 6 h / 50 - 60 °C View Scheme

1: 81 percent / water / 16 h 2: 91 percent / acetyl chloride / 0.5 h / Heating 3: 67 percent / pyridine / tetrahydrofuran / 1.) room temperature, 40 min, 2.) reflux, 1 h 4: 91 percent / 0.17 h / 140 - 150 °C 5: 70 percent / sodium borohydride / 1 h / Heating 6: 80 percent / aluminium chloride / nitrobenzene / 6 h / 50 - 60 °C View Scheme

1: 91 percent / 0.17 h / 140 - 150 °C 2: 70 percent / sodium borohydride / 1 h / Heating 3: 80 percent / aluminium chloride / nitrobenzene / 6 h / 50 - 60 °C View Scheme

1: 1.) lithium diisopropylamide (LDA) / 1.) THF, -78 deg C, 10 min, 2.) THF, from -78 deg C to 0 deg C, 2 h 2: 72 percent / AlCl3 / CH2Cl2 / Ambient temperature View Scheme

in diethyl ether T=-10°C;