Multi-step reaction with 11 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -40 °C
1.2: 5 h / -40 - 0 °C
2.1: potassium carbonate / tetrahydrofuran; water / 0.17 h / 0 °C
3.1: hydrogenchloride; titanium(III) chloride; sodium acetate; zinc / methanol; dichloromethane; water / 24 h / -50 °C / Inert atmosphere
4.1: triethylamine; mercury dichloride / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
5.1: monochloromethanesulfonyl chloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C
7.1: 20 % Pd(OH)2/C; hydrogen / methanol / 3 h / 20 °C
8.1: triethylamine; mercury dichloride / N,N-dimethyl-formamide / 2 h / 20 °C
9.1: pyridine / 3 h / 20 - 50 °C
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 5 h / 20 °C
11.1: dichloromethane / 1 h / 0 °C / Inert atmosphere
11.2: 3 h / 0 - 20 °C / Inert atmosphere
With
pyridine; hydrogenchloride; titanium(III) chloride; monochloromethanesulfonyl chloride; 20 % Pd(OH)2/C; tetrabutyl ammonium fluoride; hydrogen; sodium acetate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury dichloride; zinc;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/chem.201101058