1: 75 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 2 h 2: 1.) NaH / 1.) a) petroleum ether, THF, RT, 30 min, b) 60 deg C, 1 h, 2.) reflux, 36 h 3: 90 percent / HCl gas / CHCl3; methanol / 0.75 h / Ambient temperature 4: triethylamine / benzene / 2 h / Ambient temperature 5: 0.115 g / acetonitrile / 24 h / 65 °C View Scheme

With  lithium aluminium tetrahydride in  diethyl ether  1.) 0 deg C, 30 min, 2.) RT, 2 h;   

Multi-step reaction with 2 steps 1: 75 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 2 h2: 1.) NaH / 1.) a) petroleum ether, THF, RT, 30 min, b) 60 deg C, 1 h, 2.) reflux, 36 h  

Multi-step reaction with 4 steps 1: 75 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 2 h2: 1.) NaH / 1.) a) petroleum ether, THF, RT, 30 min, b) 60 deg C, 1 h, 2.) reflux, 36 h3: 90 percent / HCl gas / CHCl3; methanol / 0.75 h / Ambient temperature4: triethylamine / benzene / 2 h / Ambient temperature  

Multi-step reaction with 3 steps 1: 75 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 2 h2: 1.) NaH / 1.) a) petroleum ether, THF, RT, 30 min, b) 60 deg C, 1 h, 2.) reflux, 36 h3: 90 percent / HCl gas / CHCl3; methanol / 0.75 h / Ambient temperature