Multi-step reaction with 14 steps
1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C
1.3: 4 h / 0 - 50 °C
2.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 - 20 °C
2.2: 0 - 20 °C
3.1: 2-methyl-but-2-ene; water; sodium chlorite; sodium dihydrogenphosphate / tert-butyl alcohol / 0.5 h / 20 °C
3.2: pH 1
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
5.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C
6.1: boron tribromide / dichloromethane / 0.58 h / -78 - 0 °C
6.2: 0.33 h / 20 °C
7.1: [bis(acetoxy)iodo]benzene / 1,4-dioxane / 0 - 20 °C
7.2: 0.33 h / 20 °C
8.1: dmap / dichloromethane / 0.33 h / 20 °C
9.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1 h / 0 °C
9.2: 0.5 h / 0 - 20 °C
10.1: trifluoroacetic acid / dichloromethane / 0 - 10 °C
10.2: 10 - 20 °C
11.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 °C
11.2: 0.5 h / 0 °C
12.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
12.2: 0.5 h / 0 °C
13.1: thionyl chloride; tetrabutyl-ammonium chloride / 1,2-dichloro-ethane / 1.5 h / 80 °C / Sealed
14.1: N-ethyl-N,N-diisopropylamine / 1,2-dimethoxyethane / 110 °C / Sealed
With
hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; 2-methyl-but-2-ene; oxalyl dichloride; [bis(acetoxy)iodo]benzene; tetrabutyl-ammonium chloride; water; isopropylmagnesium chloride; boron tribromide; diisobutylaluminium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium chloride; sodium nitrite;
N,N-dimethyl-formamide;
In
tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;