1: 49 percent / 99percent nitric acid, 96percent sulfuric acid / acetic anhydride / 0.17 h / -30 °C 2: 92 percent / dimethylformamide / 1 h / Ambient temperature 3: 91 percent / triethylamine, H2 / 10percent palladium on carbon / methanol / 1.5 h / 3800 Torr / Ambient temperature 4: 1.) triethylamine; 2.) 5percent HCl / 1.) CH2Cl2, refl., 30 min; 2.) 60 deg C, 3 h 5: 72 percent / pentan-1-ol / 2 h / Heating View Scheme

1: 92 percent / dimethylformamide / 1 h / Ambient temperature 2: 91 percent / triethylamine, H2 / 10percent palladium on carbon / methanol / 1.5 h / 3800 Torr / Ambient temperature 3: 1.) triethylamine; 2.) 5percent HCl / 1.) CH2Cl2, refl., 30 min; 2.) 60 deg C, 3 h 4: 72 percent / pentan-1-ol / 2 h / Heating View Scheme

1: 91 percent / triethylamine, H2 / 10percent palladium on carbon / methanol / 1.5 h / 3800 Torr / Ambient temperature 2: 1.) triethylamine; 2.) 5percent HCl / 1.) CH2Cl2, refl., 30 min; 2.) 60 deg C, 3 h 3: 72 percent / pentan-1-ol / 2 h / Heating View Scheme

1: 91.5 percent / N-bromosuccinimide / CCl4 / 4 h / Heating; Irradiation 2: 49 percent / 99percent nitric acid, 96percent sulfuric acid / acetic anhydride / 0.17 h / -30 °C 3: 92 percent / dimethylformamide / 1 h / Ambient temperature 4: 91 percent / triethylamine, H2 / 10percent palladium on carbon / methanol / 1.5 h / 3800 Torr / Ambient temperature 5: 1.) triethylamine; 2.) 5percent HCl / 1.) CH2Cl2, refl., 30 min; 2.) 60 deg C, 3 h 6: 72 percent / pentan-1-ol / 2 h / Heating View Scheme

in pentan-1-ol 2 h; Heating;

1: 1.) triethylamine; 2.) 5percent HCl / 1.) CH2Cl2, refl., 30 min; 2.) 60 deg C, 3 h 2: 72 percent / pentan-1-ol / 2 h / Heating View Scheme