1: With AlCl3, aluminium chloride in dichloromethane T=0°C; 1 h; Inert atmosphere; 2: With lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 1 h; Inert atmosphere;

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sodium tetrahydroborate in methanol 0 deg C, 1 h then room t., 12 h;

1: 1.) Mg, I2, 2.) dichloro<1,3-bis(diphenylphosphino)propane>nickel(II) / 1.) Et2O, reflux, 3 h, 2.) Et2O, reflux, 2 d 2: 94 percent / ICl / CH2Cl2 / 0.67 h / Ambient temperature 3: 1.) BuLi / 1.) hexane, Et2O, -70 deg C, 1 h, 2.) hexane, Et2O, 20 deg C, 8 h 4: 94 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

1: 1.) BuLi / 1.) hexane, Et2O, -70 deg C, 1 h, 2.) hexane, Et2O, 20 deg C, 8 h 2: 94 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

1: 1.) Mg, I2, 2.) dichloro<1,3-bis(diphenylphosphino)propane>nickel(II) / 1.) Et2O, reflux, 3 h, 2.) Et2O, reflux, 2 d 2: 94 percent / ICl / CH2Cl2 / 0.67 h / Ambient temperature 3: 1.) BuLi / 1.) hexane, Et2O, -70 deg C, 1 h, 2.) hexane, Et2O, 20 deg C, 8 h 4: 94 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

1: 94 percent / ICl / CH2Cl2 / 0.67 h / Ambient temperature 2: 1.) BuLi / 1.) hexane, Et2O, -70 deg C, 1 h, 2.) hexane, Et2O, 20 deg C, 8 h 3: 94 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

thionyl chloride in acetonitrile T=90°C; 1 h;