1: 72 percent / pyridinium chlorochromate / CH2Cl2 2: 59 percent 3: HCl / dioxane 4: LiAlH4 6: 100 percent 7: pyridine 9: 98 percent / pyridinium chlorochromate / CH2Cl2 10: 90 percent / N2H4, KOH View Scheme

1: 82 percent / pyridine / CH2Cl2 / 1) 0 deg C, 1 h; 2) 5 deg C, 12 h 2: 97.5 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 1.) (CH3)2S*BF3, 2.) hydrogen peroxide, aq. NaOH / 1) THF, room temperature, 16 h; 2) 40 deg C, 2 h View Scheme