Multi-step reaction with 8 steps
1.1: 88 percent / aq. hydrochloric acid / 48 h / Heating
2.1: 81 percent / conc. sulfuric acid; nitric acid (d=1.52) / 1.5 h / 0 °C
3.1: 88 percent / POCl3; BnEt3NCl / Heating
4.1: 99 percent / methanol / 64 h / 20 °C
5.1: 99 percent / H2 / Pd/C / methanol; tetrahydrofuran
6.1: 96 percent / NEt3 / CH2Cl2 / 0.25 h / 0 °C
7.1: TMEDA; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
7.2: CuI:dimethyl sulfide complex / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C
7.3: 53 percent / tetrahydrofuran; hexane / 14 h / -78 - 20 °C
8.1: 95 percent / aq. hydrochloric acid / H2O / 3.5 h / Heating
With
hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; nitric acid; triethylamine; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water;
1.1: Hydrolysis / 2.1: Nitration / 3.1: Chlorination / 4.1: Substitution / 5.1: Hydrogenation / 6.1: Acylation / 7.1: Metallation / 7.2: complexation / 7.3: Alkylation / 8.1: Hydrolysis;
DOI:10.1016/S0040-4020(97)00771-0