lithium aluminium tetrahydride in diethyl ether T=0 - 20°C; 18 h;

lithium aluminium tetrahydride in tetrahydrofuran 1 h; Ambient temperature;

1.1: toluene-4-sulfonic acid / toluene / Reflux; Dean-Stark trap 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 2.2: Inert atmosphere View Scheme

1: 8 g / pyridine / 7 h / 0 °C 2: 1.59 g / LiBr / tetrahydrofuran / 4 h / Heating 4: 100 percent / H2 / platinum (10percent) on carbon / ethyl acetate / 8.5 h / Ambient temperature 5: 95 percent / toluene-p-sulphonic acid / acetone; H2O / 3 h / Heating 6: 100 percent / pyridine / 48 h 7: BH3-THF / tetrahydrofuran / 0 deg C, 10 min, RT, 6 h 8: 88 percent / 5percent KOH / methanol / 48 h / Ambient temperature 9: 65 percent / pyridinium dichromate / CH2Cl2 / 60 h 10: 20 mg / K2CO3, hydrazine hydrate 85percent, triethylene glycol / 150 deg C, 1 h, 220 deg C, 5.5 h View Scheme