1: 92 percent / H2 / 10percent Pd/C / methanol / 2 h / 2280 Torr 2: 80 percent / SOCl2 / CH2Cl2 / 1.) room temp., overnight, 2.) reflux, 2 h View Scheme

1.1: H2 / Pd(OH)2 2.1: Et3N / methanol / 2 h / Heating 3.1: pyridine / CH2Cl2 / 20 °C 4.1: LiBr / acetone / Heating 5.1: sodium sulfide nonahydrate / ethanol / Heating 6.1: N-chlorosuccinimide / CCl4 / 3 h / Heating 6.2: 20 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / 20 °C 7.1: 66 percent / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 20 °C View Scheme

1: 92 percent / SOCl2 / CH2Cl2 / 1.) room temp., overnight, 2.) reflux, 2 h 2: 58 percent / Cs2CO3 / dimethylformamide / 24 h / 85 °C 3: 96 percent / HCl / methanol / 1 h / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in methanol P=2280 Torr; 2 h;

lithium aluminium tetrahydride in diethyl ether 12 h; Ambient temperature;

potassium carbonate in acetonitrile 48 h; Heating;

sodium carbonate in N,N-dimethyl-formamide 96 h; Heating;

1: 77 percent / ethanol / 120 h / Ambient temperature 2: 90 percent / LiAlH4 / diethyl ether / 12 h / Ambient temperature View Scheme

lithium aluminium tetrahydride