1: ammonia; triethylamine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere 2: ethanol / 12 h / Reflux 3: water; sodium hydroxide / 1 h / Reflux View Scheme

1: 85.8 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 83.8 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 95.5 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 4: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 5: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

thionyl chloride in N,N-dimethyl-formamide T=80°C; 1 h;

triethylamine in dichloromethane 12 h; Heating;