Multi-step reaction with 11 steps
1.1: sodium methylate / methanol / 23 h / 20 - 60 °C / Heating / reflux
1.2: 20 °C
2.1: hydrogen / 20% Pd(OH)2 on carbon / tetrahydrofuran; methanol / 27 h / 20 °C
3.1: methanol; hexane; benzene / 2.25 h / 0 - 20 °C
3.2: 0.25 h
4.1: pyridinium hydrobromide perbromide / tetrahydrofuran; dichloromethane / 2 h / 20 °C
5.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 20 - 60 °C
6.1: cesium fluoride / bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane / 20 - 120 °C
7.1: sodium hydride / dimethyl sulfoxide / 0.17 h / 20 °C
7.2: 2.33 h / 20 - 200 °C / Microwave irradiation
8.1: methanol; hexane; benzene / 1.67 h / 20 °C
9.1: potassium trimethylsilonate / tetrahydrofuran / 17 h / 20 °C
10.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C
11.1: dichloromethane / 1.5 h / 20 °C
With
oxalyl dichloride; potassium trimethylsilonate; hydrogen; sodium methylate; pyridinium hydrobromide perbromide; sodium hydride; sodium carbonate; cesium fluoride; lithium chloride;
tetrakis(triphenylphosphine) palladium(0); bis(tri-t-butylphosphine)palladium(0); 20% Pd(OH)2 on carbon; N,N-dimethyl-formamide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; benzene;