Multi-step reaction with 9 steps
1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 20 °C
2.1: aluminum (III) chloride / dichloromethane / 2 h / 0 - 20 °C
2.2: Cooling with ice
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Cooling with ice
3.2: pH 2 - 3 / Cooling with ice
4.1: sodium hydride / tetrahydrofuran / 1 h / Cooling with ice
4.2: 20 °C
5.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Sealed flask
5.2: 1 h
6.1: methanesulfonic acid / toluene; tetrahydrofuran / 20 °C
7.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 20 °C / Cooling with ice
8.1: sodium acetate / 1 h / Reflux
9.1: sodium methylate / methanol / 5 h / 20 °C
9.2: acidic resin / 20 °C
With
triethylsilane; aluminum (III) chloride; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; methanesulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium acetate; sodium hydride;
N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; dichloromethane; toluene;