Multi-step reaction with 9 steps
1.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 50 °C
1.2: 1.5 h / 0 - 50 °C / Inert atmosphere
2.1: trifluoroacetic acid; triethylsilane; trifluorormethanesulfonic acid / 2 h / 75 °C / Inert atmosphere
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
4.2: 0 - 20 °C
5.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere
5.2: 3 h / -78 - -5 °C / Inert atmosphere
5.3: 2 h / -25 - 5 °C / Inert atmosphere
6.1: acetic acid; sodium acetate; palladium dichloride / water / 1.5 h / 70 °C
7.1: Jones reagent / acetone / 6.5 h / 0 - 20 °C
8.1: hydrogen; palladium dichloride / ethyl acetate; methanol / 16 h / 2250.23 Torr / Inert atmosphere
9.1: 2,4,6-trimethyl-pyridine / 0 - 20 °C / Inert atmosphere
With
triethylsilane; lithium aluminium tetrahydride; Jones reagent; n-butyllithium; thionyl chloride; trifluorormethanesulfonic acid; hydrogen; sodium acetate; sodium hydride; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid; palladium dichloride;
In
tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; mineral oil;