Multi-step reaction with 11 steps
1: AlCl3 / 1,2-dichloro-ethane / 4 h
2: hydrazine hydrate, potassium hydroxide / ethane-1,2-diol / 20 - 160 °C
3: NaBH4, BF3*OEt2
4: 2,2,6,6-tetramethyl-1-piperidinyloxy, 5percent aq. sodium bicarbonate, 10percent aq. sodium hypochlorite / toluene / 0.5 h / 0 - 5 °C
5: triethylamine, sulfur / dimethylformamide / 4 h / 50 - 60 °C
6: 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: P2S5 / CHCl3 / 4 h / Heating
11: hydrazine hydrate / methanol / 1 h
With
2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium hydroxide; sodium hypochlorite; sodium tetrahydroborate; aluminium trichloride; tetraphosphorus decasulfide; boron trifluoride diethyl etherate; ammonia; sodium hydrogencarbonate; sulfur; hydrazine hydrate; acetic acid; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; chloroform; ethylene glycol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1016/0223-5234(96)85877-6