Multi-step reaction with 13 steps
1: 95 percent / hydrogen, quinoline / 5percent palladium on barium sulfate / ethanol / Ambient temperature
2: 96 percent / triethylamine / CH2Cl2 / 0.5 h / 0 °C
3: 1.56 g / potassium tert-butoxide / 2-methyl-propan-2-ol / 2.5 h / Ambient temperature
4: 85 percent / p-toluenesulfonic acid / benzene / 20 h / Heating
5: 64 percent / copper bronze / 1.5 h / 130 - 140 °C
6: 94 percent / lithium aluminum hydride / diethyl ether / 20 h / Ambient temperature
7: 84 percent / water, 4 N hydrochloric acid / acetone / 3 h / Ambient temperature
8: 370 mg / triethylamine / CH2Cl2 / 0.5 h / 0 °C
9: 242 mg / lithium chloride, hexamethylphosphoramide / diethyl ether
10: 141 mg / potassium tert-butoxide / tetrahydrofuran / 1.5 h / Ambient temperature
11: 88 percent / lithium triethylborohydride / tetrahydrofuran / 20 h / Ambient temperature
12: 73 percent / chromium trioxide, pyridinium hydrochloride / CH2Cl2 / 2 h / Ambient temperature
13: 81 percent / diethylene glycol, sodium, hydrazine hydrate / 1.) 180 deg C, 18 h, 2.) 210 deg C, 6 h
With
quinoline; chromium(VI) oxide; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; potassium tert-butylate; water; hydrogen; pyridine hydrochloride; sodium; copper; lithium triethylborohydride; toluene-4-sulfonic acid; hydrazine hydrate; triethylamine; lithium chloride; diethylene glycol;
Pd-BaSO4;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone; tert-butyl alcohol; benzene;