Multi-step reaction with 11 steps
1.1: sodium nitrite; acetic acid; nitric acid / 24 h / 20 °C
1.2: 60 °C
2.1: phenylmagnesium chloride / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere
2.2: 3 h / -30 - 20 °C / Inert atmosphere
2.3: Inert atmosphere
3.1: dmap / dichloromethane / 20 °C / Inert atmosphere
4.1: ethanol / Reflux
5.1: potassium carbonate; methanol / 1 h / Reflux
6.1: 0.75 h / 110 °C / Inert atmosphere
7.1: ammonium fluoride / methanol / 12 h / 50 °C
8.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C
9.1: dmap; triethylamine / dichloromethane / 20 °C / Inert atmosphere
10.1: ammonia / 1,4-dioxane / 90 °C / Sealed tube
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C
With
1H-imidazole; methanol; dmap; ammonium fluoride; phenylmagnesium chloride; tetrabutyl ammonium fluoride; ammonia; nitric acid; potassium carbonate; acetic acid; triethylamine; sodium nitrite;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;