1: 1.) NaH / 1.) DMF, 40 deg C, 30 min, 2.) 80 deg C, 48 h 2: 32 percent / BCl3 / CH2Cl2 / 3.5 h / -78 °C View Scheme

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