sulfuric acid T=220°C;

T=500°C;

1: SOCl2; DMAP / toluene / 1 h / Heating 2: 13.3 g / NH3(g) / CH2Cl2 / 20 °C 3: 94 percent / pyridine; TFAA / dioxane / 3 h / 20 °C 4: 99 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 20 °C 5: 99 percent / (COCl)2 / toluene / 22 h / 70 °C 6: 90 percent / NaN3 / acetone / 1.5 h / 20 °C 7: 67 percent / H2SO4 / 1 h / 0 - 20 °C View Scheme

1: 96 percent / KOH / dioxane; methanol / 2 h / 80 °C 2: SOCl2; DMAP / toluene / 1 h / Heating 3: 13.3 g / NH3(g) / CH2Cl2 / 20 °C 4: 94 percent / pyridine; TFAA / dioxane / 3 h / 20 °C 5: 99 percent / aq. LiOH / tetrahydrofuran / 1.5 h / 20 °C 6: 99 percent / (COCl)2 / toluene / 22 h / 70 °C 7: 90 percent / NaN3 / acetone / 1.5 h / 20 °C 8: 67 percent / H2SO4 / 1 h / 0 - 20 °C View Scheme

in N,N-dimethyl-formamide 2 h; Inert atmosphereReflux;

potassium carbonate in 1,4-dioxane T=20°C; 0.166667 h;

sodium tetrahydroborate; sulfuric acid in tetrahydrofuran T=20°C; 0.5 h;