Multi-step reaction with 9 steps
1: 78 percent / acetic acid; H2O / 60 °C
2: 86 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating
3: 96 percent / pyridine / 3 h / Ambient temperature
4: 74 percent / CrO3, aq. AcOH / Ambient temperature
5: 91 percent / isoamyl nitrite, HCl / diethyl ether / 1 h / Ambient temperature
6: 67 percent / H2 / 10percent Pd/C / tetrahydrofuran / 2327.2 Torr / Ambient temperature
7: NaBH4 / ethanol / 1 h / Ambient temperature
8: 1.) BH3*THF, 2.) aq. HCl / 1.) r.t., 3 h, 2.) reflux, 1 h
9: 62 percent / aq. NaOH / 1,2-dichloro-ethane / 1.) r.t., 30 min, 2.) r.t., overnight
With
pyridine; chromium(VI) oxide; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; borane-THF; hydrogen; acetic acid; isopentyl nitrite;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; water; acetic acid; 1,2-dichloro-ethane;