Multi-step reaction with 9 steps
1.1: sulfuric acid / 14 h / Dean-Stark trap; Heating
2.1: triethylamine / dmap / dichloromethane / 16 h / 20 °C
3.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane / 5.5 h / 100 °C / Inert atmosphere
4.1: lithium aluminium tetrahydride / diethyl ether; tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere
4.2: 0.5 h
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 18 h / 20 °C
6.1: titanium(IV) tetraethanolate / tetrahydrofuran / 16 h / 65 °C / Inert atmosphere
7.1: diethyl ether; tetrahydrofuran / 2.5 h / 20 °C / Cooling with acetone-dry ice; Inert atmosphere
8.1: hydrogenchloride; water / tetrahydrofuran / 1.5 h / 20 °C
9.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 19 h / 110 °C
With
hydrogenchloride; titanium(IV) tetraethanolate; potassium phosphate; lithium aluminium tetrahydride; sulfuric acid; water; triethylamine; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dmap; tris-(dibenzylideneacetone)dipalladium(0);
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; dimethyl sulfoxide; butan-1-ol;