thionyl chloride

in N-methyl-acetamide; dichloromethane

(i) H2, Raney-Ni, (ii) SOCl2; Multistep reaction;

1.1: pyridine / toluene / 16 h / |Reflux 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 2 h / -75 - -60 °C 2.2: 3 h / -78 °C 3.1: copper(l) iodide; triethylamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex / N,N-dimethyl-formamide / 12 h / 60 °C / |Inert atmosphere 4.1: hydrogenchloride / tetrahydrofuran; water / 12 h / 40 °C 5.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / -25 °C 6.1: methanol; lithium hydroxide hydrate / tetrahydrofuran / 20 °C View Scheme

1: 91 percent / LiAlH4 / diethyl ether 2: 76 percent / HBr, aq/H2SO4 3: 93 percent / dimethylsulfoxide 4: 78 percent / H2SO4 / acetic acid View Scheme

1: 91 percent / LiAlH4 / diethyl ether 2: 76 percent / HBr, aq/H2SO4 View Scheme