1: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating 2: 90 percent / conc. HCl / 1 h / 90 °C 3: Et3N / acetone / 0.25 h / 0 °C 4: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 5: 60 percent / methanol / 24 h / 20 °C View Scheme

1: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating 2: 84 percent / 3-chloroperbenzoic acid / CH2Cl2 / 8 h / 20 °C 3: 83 percent / conc. HCl / 1.33 h / 90 °C 4: Et3N / acetone / 0.25 h / 0 °C 5: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min 6: 60 percent / methanol / 24 h / 20 °C View Scheme

Multi-step reaction with 2 steps 1: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating2: 90 percent / conc. HCl / 1 h / 90 °C  

Multi-step reaction with 4 steps 1: SOCl2 / 1,2-dichloro-ethane; dimethylformamide / 0.42 h / Heating2: 90 percent / conc. HCl / 1 h / 90 °C3: Et3N / acetone / 0.25 h / 0 °C4: 1.) NaN3, 2.) 8 M HCl / 1.) Me2CO, H2O, 0 deg C, 30 min, 2.) reflux, 10 min