1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT,5 h 2: 65 percent / Na2HPO4, 6percent sodium amalgam / methanol / 2.5 h / 25 °C View Scheme

Multi-step reaction with 4 steps 1: AgNO3, N-chlorosuccinimide (NCS), 2,6-lutidine / acetonitrile; H2O / 0.17 h / Ambient temperature2: NaBH4 / H2O / 2.5 h3: 83 percent / pyridine / 0 °C4: KOH / tetrahydrofuran / 1 h / 10 °C  

Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, RT,5 h2: Na2HPO4, 6percent sodium amalgam / methanol / 2.5 h / 25 °C