1: 82 percent 2: 61 percent / Dibal-H / tetrahydrofuran 3: 65 percent / n-BuLi / tetrahydrofuran / -100 °C 4: 80 percent / pyridine hydrochloride / 0.17 h / 150 °C 5: 95 percent / H2 / Pd/C / methanol; tetrahydrofuran View Scheme

1: 94 percent / methanol / Heating 2: 62 percent / diisobutylaluminum hydride / tetrahydrofuran / 4 h / 0 °C 3: zinc iodide / 2 h / Ambient temperature 4: lithium aluminum hydride / diethyl ether / 2 h 5: 64 percent / ethanol / 6 h 6: 93 percent / pyridine hydrochloride / 0.17 h / 150 °C 7: 75 percent / H2 / 5 percent Pd/C / methanol; tetrahydrofuran / 760 Torr View Scheme

Multi-step reaction with 3 steps 1: 82 percent2: 61 percent / Dibal-H / tetrahydrofuran3: 65 percent / n-BuLi / tetrahydrofuran / -100 °C