Multi-step reaction with 11 steps
1: 93 percent / AlCl3 / 1,2-dichloro-ethane / 4 h
2: 89 percent / hydrazine hydrate, potassium hydroxide / ethane-1,2-diol / 20 - 160 °C
3: NaBH4, BF3*OEt2
4: 97 percent / CrO3, celite, pyridine / CH2Cl2 / 1.5 h / Ambient temperature
5: 70 percent / triethylamine, sulfur / dimethylformamide / 4 h / 50 - 60 °C
6: 93 percent / CHCl3 / 2 h / Heating
7: sodium iodide / tetrahydrofuran / 2 h / Heating
8: liquid ammonia / tetrahydrofuran / 4 h / -30 - 20 °C
9: acetic acid / propan-2-ol / 20 h / Heating
10: 94 percent / P2S5 / CHCl3 / 4 h / Heating
11: 91 percent / hydrazine hydrate / methanol / 1 h
With
pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; aluminium trichloride; tetraphosphorus decasulfide; Celite; boron trifluoride diethyl etherate; ammonia; sulfur; hydrazine hydrate; acetic acid; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; ethylene glycol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/0223-5234(96)85877-6