Multi-step reaction with 10 steps
1.1: triethylamine; formic acid / palladium 10% on activated carbon / 120 h / 0 - 80 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
2.2: 3 h / 0 °C
3.1: bromine; pyridine / dichloromethane / 2 h / 0 °C
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 25 °C
6.1: copper(I) bromide; sodium / N,N-dimethyl-formamide / 5 h / Inert atmosphere; Reflux
7.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 0.08 h / 0 °C
7.2: 12.25 h / 0 - 25 °C
8.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C
8.2: 1 h / -78 °C
9.1: Dess-Martin periodane / dichloromethane / 2 h / 25 °C
10.1: tetrahydrofuran / 1 h / 0 °C
With
pyridine; n-butyllithium; formic acid; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; bromine; sodium; sodium hydride; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;