Multi-step reaction with 6 steps
1: 98.5 percent / 86percent KOH / ethanol / 2 h / Heating
2: 1.) SOCl2, 2.) NH3 (gas) / 1.) reflux, 3 h, 2.) THF, RT, 3 h
3: LiAlH4 / diethyl ether / a) RT, 10.5 h, b) reflux, 4 h
4: 1.) SOCl2, HMPA, 2.) Et3N / 1.) -5 deg C, 10 min, 2.) Et2O, RT, overnight
5: 58 percent / CrO3 / acetic acid; H2O / Ambient temperature
6: 21.8percent HBr / acetic acid / 1.5 h / Ambient temperature
With
chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; ammonia; hydrogen bromide; triethylamine;
In
diethyl ether; ethanol; water; acetic acid;
DOI:10.1021/jm00181a013