1: 60 percent / Na/Hg, H2, Pd/C / methanol / 48 h / 25 °C 2: 65 percent / CsF / tetrahydrofuran / 3 h / Heating View Scheme

With  sodium amalgam; palladium on activated charcoal; hydrogen in  methanol T=25°C; 48 h;   

With  triethylamine in  dichloromethane T=0°C; 1 h;   

Multi-step reaction with 5 steps 1: 98 percent / LiAlH4 / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 30 min2: 85 percent / MCPBA / CH2Cl2 / 2 h / Ambient temperature3: 95 percent / DMAP, Et3N / CH2Cl2 / 1) 0 deg C 1 h, 2) r.t., 1 h4: 20 percent / n-BuLi / tetrahydrofuran / 1) -78 deg C, 0.5+0.5 h, 2) r.t., 1 h5: 85 percent / NEt3 / CH2Cl2 / 1 h / 0 °C  

Multi-step reaction with 2 steps 1: 20 percent / n-BuLi / tetrahydrofuran / 1) -78 deg C, 0.5+0.5 h, 2) r.t., 1 h2: 85 percent / NEt3 / CH2Cl2 / 1 h / 0 °C