Multi-step reaction with 10 steps
1.1: magnesium / diethyl ether / Inert atmosphere; Reflux
1.2: 0 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 0.25 h / 20 °C / Inert atmosphere
2.2: 1 h / 20 °C / Inert atmosphere
2.3: 0 °C
3.1: n-butyllithium / tetrahydrofuran; hexane; N,N-dimethyl-formamide / 2 h / -80 - 20 °C / Inert atmosphere
3.2: 0 °C / Inert atmosphere
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux
4.2: 0 °C
5.1: thionyl chloride; calcium carbonate; calcium chloride / diethyl ether / 12 h / 20 °C
6.1: dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere
7.1: hydrogenchloride; water / 3 h / Reflux
8.1: sodium hydroxide / ethanol; water / 2 h / Reflux
8.2: 0 °C
9.1: thionyl chloride / 1 h / 60 °C
10.1: tetrahydrofuran / 12 h / 0 - 20 °C / Reflux
With
hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; water; magnesium; trifluoroacetic acid; calcium carbonate; calcium chloride; sodium hydroxide;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm3013008