1: diisobutylaluminum hydride / diethyl ether / 1.5 h / -10 °C 2: 43 percent / pyridine / diethyl ether / 12 h / Ambient temperature; 1) 5 deg C, 1 h 2) room temperature 12 h 3: CuI, 2,2'-bipyridyl / 2 deg C, 2 h, THF View Scheme

Dess-Martin periodane in dichloromethane T=20°C; 1.5 h;

1: Li2CuCl4 / 1) THF -78 deg C, 2 hours 2) room temperature 15 h 2: 11.7 g / 5percent aq. HCl / acetone / 6 h / Ambient temperature View Scheme

1: 99.5 percent / pyridine / 15 h / -10 °C 2: Li2CuCl4 / 1) THF -78 deg C, 2 hours 2) room temperature 15 h 3: 11.7 g / 5percent aq. HCl / acetone / 6 h / Ambient temperature View Scheme

1: Li2CuCl4 / 1) THF -78 deg C, 2 hours 2) room temperature 15 h 2: 11.7 g / 5percent aq. HCl / acetone / 6 h / Ambient temperature View Scheme

1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: 99.5 percent / pyridine / 15 h / -10 °C 3: Li2CuCl4 / 1) THF -78 deg C, 2 hours 2) room temperature 15 h 4: 11.7 g / 5percent aq. HCl / acetone / 6 h / Ambient temperature View Scheme

hydrogenchloride in acetone 6 h; Ambient temperature;