samarium(III) trifluoromethanesulfonate T=20°C; 0.166667 h;

4-(N,N-dimethlyamino)pyridine; triethylamine in dichloromethane T=0 - 20°C; Inert atmosphere;

1: SnCl4, Bu3N / 1,2-dichloro-ethane / Heating 2: pyridine View Scheme

T=300°C;

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 83 percent / thionyl chloride; NaOEt / ethanol / 2 h / Heating 2: 46 percent / titanium tetraisopropoxide; cyclohexylmagnesium chloride / tetrahydrofuran; diethyl ether / 1 h / 20 °C 3: ferric(III) chloride; pyridine / diethyl ether / 3 h / 0 °C 4: sodium acetate / methanol / 20 °C View Scheme

1: (i) aq. H2O2, (ii) aq. NaOH 2: aq. HIO4 View Scheme