Multi-step reaction with 7 steps
1.1: sodium methylate / methanol / 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 60 °C / Inert atmosphere
3.1: di(n-butyl)tin oxide / toluene / Inert atmosphere; Reflux
3.2: 20 h / 20 °C / Inert atmosphere
4.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere
4.2: 20 °C / Inert atmosphere
5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 - 20 °C / Inert atmosphere
6.1: oxalyl dichloride; dimethyl sulfoxide / tetrahydrofuran / 2 h / -60 - -40 °C / Inert atmosphere
6.2: 2 h / -78 - 20 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere
7.2: -78 - 20 °C / Inert atmosphere
With
n-butyllithium; oxalyl dichloride; sodium methylate; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
6.1: |Swern Oxidation;
DOI:10.1016/j.tet.2013.04.094