Multi-step reaction with 9 steps
1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere
1.2: 2 h / -78 - 25 °C / Inert atmosphere
2.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 3.33 h / 0 - 25 °C / Inert atmosphere
3.1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 1 h / Inert atmosphere; Reflux
4.1: pyridine / dichloromethane / 1.5 h / -5 - 25 °C / Inert atmosphere
5.1: 2 h / 65 °C / Inert atmosphere
6.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride / mineral oil / 24 h / 5 - 25 °C / Inert atmosphere
7.1: barium hydroxide octahydrate / methanol / 4 h / Inert atmosphere; Reflux
8.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / 20 - 25 °C / Inert atmosphere
9.1: methylmagnesium bromide / tetrahydrofuran; diethyl ether / 0 °C / Inert atmosphere
9.2: 24 h / 0 - 25 °C / Inert atmosphere
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; thionyl chloride; oxalyl dichloride; barium hydroxide octahydrate; methylmagnesium bromide; sodium hydride; diisobutylaluminium hydride; N,N-dimethyl-formamide;
In
tetrahydrofuran; methanol; 2-methyl-but-2-ene; diethyl ether; dichloromethane; water; mineral oil; tert-butyl alcohol;
DOI:10.1002/asia.201100338