1: 100 percent / Et3N / CH2Cl2 / 0.17 h / -5 - 0 °C 2: 74 percent / LiN3, P(NMe2)3 / dimethylsulfoxide / Ambient temperature 3: H2 / Lindlar's catalyst / butan-1-ol / 3 h / 760 Torr 4: Et3N / butan-1-ol / 20 h / Heating 5: conc. HCl / 42 h / Ambient temperature 6: 70 percent / liquid NH3 / methanol / 18 h / 60 °C 7: 50 percent / 1 M BCl3 / CH2Cl2; hexane / 2.5 h / -75 °C View Scheme