1: With diisobutylaluminium hydride in dichloromethane T=-78 - 20°C; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water T=-78°C;

1: 92.3 percent / LiAlH4 / ethanol; diethyl ether / 0.5 h / 0 - 5 °C 2: 71.8 percent / PBr3, pyridine / diethyl ether / 1) overnight, 2) reflux, 0.5 h 3: 1) Mg / 2) Li2CuCl4 / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h 4: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature 5: 62 percent / PCC / CH2Cl2 / 1 h / Ambient temperature View Scheme

1: With diisobutylaluminium hydride in dichloromethane T=-78 - 20°C; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water T=-78°C;