Multi-step reaction with 12 steps
1: 1) NaH / 1) DMF, 2) DMF, 65 deg C, 3 h
2: 93.7 percent / H2 / 10percent Pd/C / ethanol / 24 h / 55 °C / 2280 Torr
3: 75 percent / pyridine / 2 h / 0 °C
4: 98 percent / dimethylformamide / 3 h / 60 °C
5: 53 percent / AlCl3 / CS2 / Heating
6: 78 percent / HOAc, NH4OAc / benzene / 48 h / Heating
7: 43 percent / CuCl / tetrahydrofuran; diethyl ether / Ambient temperature
8: KOH, H2O / ethane-1,2-diol / 36 h / Heating
9: 6 h / 180 °C
10: diethyl ether
11: 65 percent / HNO3, Ac2O / CH2Cl2 / 0.33 h / -15 °C
12: 89 percent / H2 / 10percent Pd/C / ethyl acetate
With
pyridine; potassium hydroxide; aluminium trichloride; ammonium acetate; water; hydrogen; nitric acid; acetic anhydride; sodium hydride; acetic acid; copper(l) chloride;
palladium on activated charcoal;
In
tetrahydrofuran; carbon disulfide; diethyl ether; ethanol; dichloromethane; ethylene glycol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1002/mrc.1260300807