Multi-step reaction with 8 steps
1: 1.) Na / 1.) EtOH, 2.) EtOH, reflux, 10 h
2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 60 deg C, 10 h
3: NaN3, NaI, 18-crown-6 / dimethylformamide / 18 h / 60 °C
4: Ph3P, H2O / tetrahydrofuran / 62 h / Ambient temperature
5: 6N HCl / acetic acid / 18 h / Heating
6: SOCl2 / 18 h / Heating
7: Et3N / CH2Cl2 / 18 h
8: diisobutylaluminum hydride / CH2Cl2; toluene / 0.08 h / -78 °C
With
hydrogenchloride; thionyl chloride; sodium azide; 18-crown-6 ether; water; sodium; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; sodium iodide;
In
tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00101a015