Multi-step reaction with 17 steps
1.1: chromium(VI) oxide; sulfuric acid; acetic acid / water / 3 h / 100 °C
2.1: triethylamine / dmap / dichloromethane / 2 h / 10 - 20 °C
3.1: iron; ammonium chloride / ethanol; water / 1 h / 95 °C
4.1: sodium hydrogencarbonate / tetrahydrofuran / 19 h / 0 - 50 °C
5.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C
7.1: Burgess Reagent / tetrahydrofuran / 3 h / 75 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 0 °C
8.2: 0.5 h / 0 °C
9.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C
10.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
10.2: -78 - 20 °C
11.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 0 °C
12.1: sodium azide / N,N-dimethyl-formamide / 2 h / 75 °C
13.1: water; acetic acid / tetrahydrofuran / 16 h / 20 °C
14.1: thionyl chloride / dichloromethane / 0.5 h / 0 - 20 °C
15.1: potassium carbonate / acetonitrile / 20 h / 85 °C
16.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
16.2: 1.5 h / 75 °C
17.1: pyridine / tetrahydrofuran / 0.5 h / 0 °C
With
pyridine; 1H-imidazole; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; sodium azide; Burgess Reagent; sulfuric acid; water; iron; sodium hydrogencarbonate; potassium carbonate; ammonium chloride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid;
dmap;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;