Multi-step reaction with 10 steps
1: NaBH4 / methanol; H2O / 1.5 h / 0 °C
2: 1.) lead tetra-acetate, iodine, 2.) Jones' chromic acid reagent / .) cyclohexane, reflux, irradiated, 1.5 h, 2.) acetone, 0 deg C, 1 h
3: potassium carbonate / methanol; H2O / 1 h / Heating
4: toluene-p-sulphonic acid monohydrate / tetrahydrofuran / 1.5 h / Ambient temperature
5: 7 percent / zinc borohydride / 1,2-dimethoxy-ethane / 1.5 h / Heating
6: 73 percent / pyridine / 24 h / Ambient temperature
7: 1.) chloroform, 2.) 2,3-dihydropyran, toluene-p-sulphonic acid / 1.) room temperature, 30 min, 2.) THF, room temperature, 6 h
8: 72 percent / LiAlH4 / tetrahydrofuran / 4 h / Ambient temperature
9: 83 percent / CrO3, pyridine / CH2Cl2 / 24 h / Ambient temperature
10: 1.0 M HCl / tetrahydrofuran / 24 h / Ambient temperature
With
pyridine; 3,4-dihydro-2H-pyran; chromium(VI) oxide; lead(IV) acetate; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; chloroform; zinc borohydride; iodine; chromic acid; potassium carbonate; toluene-4-sulfonic acid;
In
tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water;