2: 56 percent / 4-dimethylaminopyridine / CH2Cl2 / 21 h / 0 - 4 °C 3: 85 percent / tributyltin hydride, di-tert-butyl peroxide / 7.5 h / 50 °C 4: 86 percent / diisobutylaluminum hydride, 2,6-di-tert-butyl-4-methylphenol / toluene / -78 deg C to -20 deg C for 2h and then -20 deg C 1.7h 5: 96 percent / H2 / Lindlar / benzene; cyclohexane; cyclohexene / 13 h / 26 °C / 760 Torr 6: 100 percent 7: 95 percent / (n-C4H9)4NF / tetrahydrofuran / 3 h / 26 °C 8: 20percent NaOH-H2O / 18.3 h / 16 °C 9: Jones reagent / 0.33 h / -30 °C 10: CH3COOH / H2O; tetrahydrofuran / 16 deg C for 1h and 27 deg C for 29h View Scheme

2: 68 percent / 4-dimethylaminopyridine / CH2Cl2 / 3 h / 18 °C 3: 98 percent / tributyltin hydride, di-t-butyl peroxide / 0.58 h / 50 °C 4: 87 percent / H2, 5percent Pd/BaSO4, quinoline / benzene; cyclohexane / 4.5 h / 40 °C / 760 Torr 5: 98 percent / hydrogen fluoride, pyridine / 3 h / 24 °C View Scheme

2: 68 percent / 4-dimethylaminopyridine / CH2Cl2 / 3 h / 18 °C 3: 98 percent / tributyltin hydride, di-t-butyl peroxide / 0.58 h / 50 °C 4: 87 percent / H2, 5percent Pd/BaSO4, quinoline / benzene; cyclohexane / 4.5 h / 40 °C / 760 Torr 5: 87 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol 6: 85 percent / acetic acid; H2O; tetrahydrofuran / 1.5 h / 55 °C View Scheme

2: pyridine / 0 - 5 °C 3: pyridine / 0 - 5 °C 4: 42 percent / m-chloroperbenzoic acid / -78 - 20 °C 5: 89 percent / hydrogen / Lindlar catalyst / 15 h / 21 °C View Scheme