1: DIBAL / toluene / 2 h / 20 °C View Scheme

1: 89 percent / 6 M aq. NaOH / methanol / 1 h / Heating 2: tetrahydrofuran; diethyl ether / 1.) -70 deg C, 1 h, 2.) 0 deg C, 30 min 3: p-TsOH*H2O / toluene / 0.5 h / Heating 4: 76 percent / LiAlH4 / diethyl ether / 0.5 h / Ambient temperature 5: 45 percent / p-TsOH*H2O / nitromethane / 0.08 h / 40 °C View Scheme