Multi-step reaction with 13 steps
1: 1.09 g / 1.0 N aq. H2SO4 / 4 h / 50 °C
2: 1.37 g / 4-dimethylaminopyridine (DMAP), Et3N / CH2Cl2 / 1.5 h
3: 860 mg / NaH / dimethylsulfoxide / 20 h / Ambient temperature
4: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature
5: 4-dimethylaminopyridine, Et3N / CH2Cl2 / Ambient temperature
6: NaN3 / tetrahydrofuran; dimethylformamide / 2 h
7: OsO4, NaIO4 / tetrahydrofuran; H2O
8: NaBH4 / methanol / 0.75 h / 0 °C
9: 163 mg / 2.5 h / Ambient temperature
10: 93 percent / 4-dimethylaminopyridine (DMAP), Et3N / CH2Cl2 / 1.83 h / Ambient temperature
11: 70 percent / LiBr / acetone / 0.42 h / Heating
12: 78 percent / NaHCO3 / acetonitrile / 14 h / Heating
13: 75 percent / 48percent HBr / 5.5 h / 150 °C
With
dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium azide; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen bromide; sodium hydride; sodium hydrogencarbonate; triethylamine; lithium bromide;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.3891/acta.chem.scand.46-0060