1: thionyl chloride / CHCl3 / 0 - 20 °C 2: 1.) LDA / 1.) THF, -5 deg C, 30 min, 2.) THF, from -5 deg C to RT, overnight 3: 62 percent / 3 N aq. HCl / Heating View Scheme

1: thionyl chloride / CHCl3 / 0 - 20 °C 2: 1.) LDA / 1.) THF, -5 deg C, 30 min, 2.) THF, from -5 deg C to RT, overnight 3: 62 percent / 3 N aq. HCl / Heating 4: 77 percent / LiAlH4 View Scheme