Multi-step reaction with 11 steps
1: tetrahydrofuran / 4 h / Heating
2: 0.5 h / Heating; reflux with 98percent HCOOH
3: 79 percent / 1 N HCl / acetone / 2 h / Heating
4: 87 percent / Jones reagent (CrO3) / acetone; H2O / 3.5 h / 15 °C
5: 92 percent / 50 percent NaH in paraffin / tetrahydrofuran / 0.17 h / 25 °C
6: 96 percent / H2 / 10 percent Pd/C / ethanol / 30 h / 25 °C / 2068.6 Torr
7: 95 percent / 30 percent H2O2, 0.2 M aq. NaOH / methanol; dimethylsulfoxide / 12 h / 50 - 55 °C
8: 100 percent / 1.) LiAlH4 2.) HCl gas / tetrahydrofuran / 24 h / Heating
9: 95 percent / HCl / methanol / 12 h
10: 89 percent / sodium thiosulfate / methanol; H2O / 0.5 h / 80 - 85 °C
11: 65 percent / thiourea, 1 N HCl / propan-2-ol / 10 h / 95 - 100 °C
With
chromium(VI) oxide; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; hydrogen; dihydrogen peroxide; sodium hydride; sodium thiosulfate; thiourea;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; water; dimethyl sulfoxide; isopropyl alcohol; acetone;
DOI:10.1016/S0040-4020(01)90332-1