Multi-step reaction with 10 steps
1.1: sodium methylate / methanol / 18.16 h / 22 °C / Heating / reflux
2.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran; methanol / 18 h / 20 °C / 2844.39 Torr
3.1: thionyl chloride / 18 h / Heating / reflux
4.1: pyridinium hydrobromide perbromide / tetrahydrofuran; chloroform / 2 - 2.66 h / 0 - 20 °C
5.1: methanol; lithium hydroxide; water / tetrahydrofuran / 2 - 3 h / 90 °C
5.2: 1 h / 0 - 20 °C
6.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 - 2.16 h / 22 - 50 °C
6.2: 21 - 24 h / 20 - 30 °C
7.1: sodium carbonate; lithium chloride / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 20.42 h / 70 °C
8.1: hydrogenchloride; water / tetrahydrofuran / 16 h / 20 °C
9.1: caesium carbonate / N,N-dimethyl-formamide / 20 h / 55 °C
10.1: methanol; sodium hydroxide; water / tetrahydrofuran / 0.5 h / 85 °C / microwave irradiation
With
hydrogenchloride; methanol; lithium hydroxide; sodium hydroxide; thionyl chloride; water; hydrogen; sodium methylate; sodium carbonate; caesium carbonate; pyridinium hydrobromide perbromide; 1,1'-carbonyldiimidazole; lithium chloride;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; ethanol; chloroform; water; N,N-dimethyl-formamide; toluene;