1: 52 percent / lithium aluminium hydride / tetrahydrofuran 2: 72 percent / H2 / 5 percent palladised charcoal / methanol / 20 h 3: 86 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature 4: triethylamine / tetrahydrofuran; CCl4 / 2 h / Ambient temperature 5: 25 percent / sodium metal / liquid ammonia View Scheme

With  lithium aluminium tetrahydride in  tetrahydrofuran  

Multi-step reaction with 3 steps 1: 52 percent / lithium aluminium hydride / tetrahydrofuran2: 72 percent / H2 / 5 percent palladised charcoal / methanol / 20 h3: 86 percent / boron tribromide / CH2Cl2 / 2 h / Ambient temperature