1: lithium aluminium tetrahydride / diethyl ether / 4.5 h / 0 - 20 °C / Inert atmosphere 2: pyridine; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere View Scheme

1: With N,N,N',N',N'',N''-hexamethylphosphoric triamide; n-butyllithium; N-ethyl-N,N-diisopropylamine in tetrahydrofuran; hexane T=-78 - -10°C; 0.833333 h; Inert atmosphere; 2: ethyl 2,4-hexadienoate in tetrahydrofuran; hexane 0.333333 h; Inert atmosphere;

triethylamine in dichloromethane 1.) 45 min, 2.) room temperature, 4 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

triethylamine

tetrachloromethane