Multi-step reaction with 8 steps
1.1: sodium hydroxide / toluene / 1 h
2.1: toluene-4-sulfonic acid / toluene / 16 h / Reflux; Water separator
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C
3.2: 12 h / 20 °C
4.1: sodium hydroxide; methanol / 3 h / 20 °C
4.2: pH 2
5.1: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
5.2: 2.5 h / 20 °C
6.1: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 15 h / 80 °C / 1500.15 Torr
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere
8.1: 4-methylmorpholine N-oxide / tetrapropylammonium perruthennate / dichloromethane / 12 h / 20 °C / Molecular sieve
With
methanol; lithium aluminium tetrahydride; sodium hydride; 4-methylmorpholine N-oxide; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; sodium hydroxide;
tetrapropylammonium perruthennate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; toluene-4-sulfonic acid;
In
tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil;