Multi-step reaction with 8 steps
1: CrO3, conc. H2SO4, Ac2O / ethanol; H2O / 1 h / Heating
2: 61 percent / NaH, CuBr*Me2S / nitrobenzene / 7 h / 110 °C
3: 75 percent / t-BuOK / CH2Cl2 / 2 h / -60 °C
4: 98 percent / H2 / 10percent Pd-C / methanol / 10 h / 25 °C
5: 86 percent / DMAP, pyridine / CH2Cl2 / 3 h / 0 °C
6: 88 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 10 h / 0 °C
7: 1.) 1-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) CH2Cl2, 0 deg C, 2.) 25 deg C, 1 h
8: 90 percent / n-Bu4NF / tetrahydrofuran; dimethylformamide / 2 h / 25 °C
With
pyridine; chromium(VI) oxide; dmap; lithium hydroxide; copper(I) bromide dimethylsulfide complex; sulfuric acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; acetic anhydride; sodium hydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; nitrobenzene; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61289-3