Multi-step reaction with 17 steps
1.1: bromine; acetic acid / methanol / 2 h / 20 °C / Cooling with ice
2.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C
2.2: 4 h / 0 - 50 °C
3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / -78 - 20 °C
3.2: 1 h / 20 °C
4.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C
4.2: pH 1
5.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
6.1: triethylamine / dmap / 1 h / 20 °C
7.1: boron tribromide / dichloromethane / 0.58 h / -78 - 0 °C
7.2: 0.33 h / 20 °C
8.1: potassium carbonate / acetone / 20 °C
9.1: n-butyllithium / tetrahydrofuran; hexanes / -100 - -96 °C
9.2: 1 h / -92 - -78 °C
9.3: 0 °C
10.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C
11.1: methanol; sodium tetrahydroborate / dichloromethane / 1.08 h / 0 - 20 °C
12.1: dmap / dichloromethane / 20 °C
13.1: iodine; silver trifluoroacetate / chloroform / 20 °C
14.1: copper(l) iodide / N,N-dimethyl-formamide / 72 h / 80 °C / Sealed flask
15.1: hydrogenchloride / 1,4-dioxane / 20 °C
15.2: 20 °C
16.1: potassium carbonate / acetone / 3 h / 20 - 50 °C
17.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine; diisopropylamine / tetrahydrofuran; hexanes / 0.67 h / -78 - -70 °C
17.2: -100 - -90 °C
With
hydrogenchloride; methanol; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; n-butyllithium; 2-methyl-but-2-ene; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; bromine; iodine; silver trifluoroacetate; boron tribromide; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; diisopropylamine; trifluoroacetic acid; sodium nitrite;
dmap; N,N-dimethyl-formamide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexanes; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;