Multi-step reaction with 11 steps
1.1: toluene / 24 h / Dean-Stark; Reflux
2.1: sodium hydroxide; tetrabutyl-ammonium chloride / water; dichloromethane / 0 - 20 °C
3.1: triethylsilane; titanium tetrachloride / dichloromethane / Inert atmosphere; Reflux
4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 h / 20 °C
5.1: sodium dihydrogenphosphate; sodium chlorite / water; acetonitrile; tert-butyl alcohol / 20 °C
6.1: tributylphosphine / dichloromethane / 16 h / Reflux
7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / Reflux
8.1: lithium borohydride / diethyl ether / 48 h / Inert atmosphere; Reflux
9.1: sodium hydride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
9.2: 16 h / Reflux; Inert atmosphere
10.1: potassium hexamethylsilazane / tetrahydrofuran / 2 h / 20 °C
10.2: 16 h / 20 °C
11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 1 h / 20 °C
With
triethylsilane; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; 2,2'-azobis(isobutyronitrile); tributylphosphine; tetrabutyl-ammonium chloride; tri-n-butyl-tin hydride; titanium tetrachloride; potassium hexamethylsilazane; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1039/c2cc38540f