Multi-step reaction with 10 steps
1.1: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C
1.2: 81 percent / tetrahydrofuran / 0.5 h / -40 °C
2.1: 94 percent / 2 N HCl / tetrahydrofuran / 20 °C
3.1: 58 percent / resorcinol; acetate buffer; NaClO2 / dioxane; H2O / 20 °C / pH 3.8
4.1: K2CO3 / dimethylformamide / 20 °C
5.1: 4 N HCl / ethyl acetate / 20 °C
5.2: AcOH / dioxane / 6 h / Heating
6.1: 97 percent / 2 N aq. NaOH / tetrahydrofuran; methanol / 2 h / 20 °C
7.1: 74 percent / i-Pr2NEt / various solvent(s) / 8 h / 110 °C
8.1: 61 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C
9.1: 90 percent / H2 / 10percent Pd/C / tetrahydrofuran; methanol / 20 °C
10.1: 86 percent / K2CO3 / dimethylformamide / 40 °C
With
hydrogenchloride; sodium hydroxide; sodium chlorite; n-butyllithium; acetate buffer; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; recorcinol;
10percent Pd/C;
In
tetrahydrofuran; 1,4-dioxane; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm000558h