1: 90 percent / LiALH4 / tetrahydrofuran / 3.5 h / Ambient temperature 2: 91 percent / pyridine / 48 h / Ambient temperature 3: 80 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 4: 89 percent / toluene / 17 h / Heating 5: 1.) MeI, 2.) tert-BuOK / 1.) toluene, 70 deg C, 20 h, 2.) tert-BuOH, reflux, 5 h 6: 91 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 7: 88 percent / CH2Cl2 / 18 h / Ambient temperature 8: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme