1: With sodium bis(2-methoxyethoxy)aluminium dihydride in tetrahydrofuran T=20°C; 3.5 h; 2: With iodine in tetrahydrofuran; ethyl acetate T=20°C; 2 h;

1: 92 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, overnight 3: 1.) NaAlH2(OCH2CH2OEt)2 (Red-Al), 2.) I2 / 1.) THF, toluene, 0 deg C, overnight, 2.) THF, toluene, from -78 to 0 deg C View Scheme

1: 92 percent / Et3N, 4-(dimethylamino)pyridine / CH2Cl2 / 6 h / Ambient temperature 2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, overnight 3: 1.) NaAlH2(OCH2CH2OEt)2 (Red-Al), 2.) I2 / 1.) THF, toluene, 0 deg C, overnight, 2.) THF, toluene, from -78 to 0 deg C View Scheme

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, overnight 2: 1.) NaAlH2(OCH2CH2OEt)2 (Red-Al), 2.) I2 / 1.) THF, toluene, 0 deg C, overnight, 2.) THF, toluene, from -78 to 0 deg C View Scheme