aluminium trichloride in benzene T=0 - 20°C; Acylation;

pyrrolidine; tetrabutylammomium bromide; palladium diacetate in N,N-dimethyl-formamide T=100°C; 10 h; Molecular sieveInert atmosphere;

phosphorus pentoxide; benzene

tetrachlorosilane; benzene anschliessend Erwaermen mit Thiophen und Zinn(IV)-chlorid und Behandeln des Reaktionsgemisches mit Wasserdampf bei 300grad;

1.1: 56 percent / 85 percent N2H4*H2O; NaOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 2.1: 100 percent / AlCl3 / benzene / 0 - 20 °C 3.1: 44 percent / 85 percent N2H4*H2O; NaOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 4.1: 44 percent / Br2 / CHCl3 / 4 h / 0 °C 5.1: n-BuLi; S(SO2Ph)2 / diethyl ether / 45 h / -78 °C 5.2: 3.6 g / hexane / 2 h / -78 °C View Scheme

sodium hydroxide; hydrazine hydrate in diethylene glycol Reduction; 4 h; Heating;

1: hydrazine 2: phosphoryl chloride View Scheme