Multi-step reaction with 11 steps
1.1: 88 percent / POCl3 / benzene / 24 h / 20 °C
2.1: 100 percent / hydrogen; Et3N / Pd-C / ethyl acetate / 0.75 h / 20 °C
3.1: NaH / toluene / 15 h / 110 °C
3.2: 78 percent / aq. HCl / dioxane / 15 h / 70 °C
4.1: 83 percent / NaOH / ethanol; H2O / 15 h / 20 °C
5.1: 60 percent / potassium tert-butoxide / dimethylsulfoxide / 5 h / 100 °C
6.1: potassium carbonate; iodine monochloride / dimethylformamide / 16 h / 20 °C
7.1: 520 mg / Ag2CO3 / benzene / 72 h
8.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C
8.2: 134 mg / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C
9.1: diphenylphosphoryl azide; Et3N / benzene / 0.25 h / Heating
9.2: LiOH / tetrahydrofuran / 1 h / 20 °C
10.1: 85 mg / NaHCO3 / tetrahydrofuran / 0 - 20 °C
11.1: 93 percent / cerium ammonium nitrate / acetonitrile; H2O / 0.75 h / 0 °C
With
sodium hydroxide; n-butyllithium; ammonium cerium(IV) nitrate; diphenylphosphoranyl azide; potassium tert-butylate; hydrogen; Iodine monochloride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; silver carbonate; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1021/jo701435p