1: 79 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 2: 93 percent / NaIO4 / methanol; H2O / 1.5 h / 0 °C 3: 1) n-BuLi / 1) THF, hexane, -78 deg C, 15 min, 2) THF, hexane, -78 deg C, 30 min 4: 1) SOCl2, pyridine, 2) LiAlH4 / 1) THF, -10 deg C, 45 min, 2) THF, RT, 15 min then reflux, 30 min View Scheme

1: LiAlH4 / tetrahydrofuran / 1 h / Heating 2: 1.) NaIO4, 2.) NaBH4 / 1.) MeOH, 3-5 deg C View Scheme