Multi-step reaction with 11 steps
1.1: toluene / 14 h / 90 °C
1.2: 20 h / 80 °C
2.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 1 h / 20 °C
3.1: thionyl chloride / toluene / 2.5 h / 100 °C
3.2: 14 h / 20 °C
4.1: Lawessons reagent / tetrahydrofuran / 0.33 h / 60 °C
5.1: ethanol / 14 h / 90 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C
7.1: sulfur trioxide pyridine complex / dimethyl sulfoxide / 14 h / 20 °C
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 - 20 °C
8.2: 5 h / 0 - 20 °C
9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 3 h / 0 - 60 °C
10.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 14 h / 20 °C
11.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C / 760.05 Torr
With
Lawessons reagent; lithium aluminium tetrahydride; thionyl chloride; palladium 10% on activated carbon; water; hydrogen; sulfur trioxide pyridine complex; sodium hydride; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;