Multi-step reaction with 14 steps
1.1: triethylamine / tetrakis(triphenylphosphine) palladium(0) / acetonitrile / 15 h / Heating / reflux
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2.2: 0 °C
3.1: thionyl chloride / dichloromethane / 0 - 20 °C
4.1: dimethyl sulfoxide / 20 °C
5.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / water / 70 °C
6.1: sodium hydroxide; water / 2.5 h / Heating / reflux
7.1: thionyl chloride / N,N-dimethyl-formamide / 2 h / 20 °C
8.1: triethylamine / dichloromethane / 18 h / 20 °C
9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 80 °C
10.1: dichloromethane / 3.5 h / 20 °C
11.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 0.5 h / 20 °C
12.1: dichloromethane / 20 °C
13.1: acetone / 1.5 h
14.1: hydrogenchloride / methanol / 1 h / 60 °C
With
hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; N-benzyl-N,N,N-triethylammonium chloride; water; sodium carbonate; triethylamine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; acetonitrile;