Multi-step reaction with 11 steps
1.1: boron tribromide / dichloromethane / 12.33 h / -40 - 20 °C
2.1: triethylamine; magnesium chloride / tetrahydrofuran / 0.25 h / 160 °C / Microwave irradiation
2.2: 2 h / Heating / reflux
3.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 20 °C
3.2: 20 °C
4.1: sodium hydroxide; hydroxylamine hydrochloride / tetrahydrofuran; methanol; water / 1 h / 20 °C / pH 9
5.1: hydrogenchloride; sodium cyanoborohydride; methyl red / tetrahydrofuran; methanol; water / 12 h / pH 3
5.2: pH 9
6.1: calcium chloride / diethyl ether / 3 h / 20 °C
7.1: titanium(IV) isopropylate / tetrahydrofuran / 0.25 h / 140 °C / Microwave irradiation
7.2: 20 °C
8.1: hydrogenchloride / tetrahydrofuran; water / 2 h / 20 °C
9.1: trimethylaluminum / hexane; dichloromethane / 1 h / 20 °C
9.2: 12 h / 20 °C
9.3: 2 h / 20 °C
10.1: potassium acetate; caesium carbonate / dimethyl sulfoxide / 0.17 h
10.2: 4 h / 70 °C
11.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane / 0.17 h / 20 °C
11.2: 2 h / 20 °C
With
titanium(IV) isopropylate; hydrogenchloride; sodium hydroxide; hydroxylamine hydrochloride; trimethylaluminum; potassium acetate; boron tribromide; sodium cyanoborohydride; potassium carbonate; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; methyl red; calcium chloride; magnesium chloride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;