lithium aluminium tetrahydride; titanium(III) chloride in tetrahydrofuran T=20°C; McMurry reaction;

1: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C 2: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min 3: 2 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature View Scheme

Multi-step reaction with 2 steps 1: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C2: 1.) DIBAH; 2.) MnO2 / 1.) THF, 0 deg C, 15 min; 2.) Et2O, room temperature, 30 min  

With  manganese(IV) oxide; sodium carbonate in  dichloromethane T=0 - 25°C; 0.5 h;  Inert atmosphere;