1: 75 percent / 2 h / 155 - 160 °C 2: 59 percent / O3 / CHCl3 / 0.5 h / -40 °C 3: 89 percent / N2H4*H2O / Raney-nickel / dioxane; ethanol / 1.) 50 deg C, 1 h; 2.) reflux, 30 min 4: 82 percent / pyridine / 1.) 0 deg C, 1 h; 2.) 20 deg C, 2 h View Scheme

1: 92 percent / H2 / Raney-nickel / methanol / 4 h / 52504.2 Torr 2: 94 percent / pyridine / 1./ 3 h. 0 deg C. 2./ room temp. overnight. View Scheme