Multi-step reaction with 9 steps
1: 1.) Mg / 1.) THF, 2.) THF, room temp., 30 min, 50-55 deg C, 1 h
2: oxalic acid / toluene / 16 h / Heating
3: 1.) NaBH4, BF3*Et2O, 2.) 10percent NaOH, 30percent H2O2 / 1.) THF, room temp., 15 h, 2.) THF, H2O, room temp., 1 h
4: 33.6 percent / Na2Cr2O7*2H2O, conc. H2SO4 / diethyl ether; H2O / 2 h / 5 - 13 °C
5: 75.8 percent / TiCl4 / benzene / 1.) room temp., overnight, 2.) 75-80 deg C, 8 h
6: 78 percent / benzene / 20 h / Heating
7: 90.3 percent / NH2OH*HCl, NaOAc / dimethylformamide / Ambient temperature
8: 81.9 percent / LiAlH4 / tetrahydrofuran; dioxane / Heating
9: 97.7 percent / 5percent NaHCO3 / CH2Cl2 / 3 h / Ambient temperature
With
sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium dichromate; sulfuric acid; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; dihydrogen peroxide; sodium acetate; oxalic acid; titanium tetrachloride; sodium hydrogencarbonate; magnesium;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1248/cpb.28.1022