1: 1,8-diazabicyclo[5.4.0]undec-7-ene / diethyl ether / 0.5 h / 20 °C / |Inert atmosphere 2: copper(l) iodide; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.25 h / -20 - 0 °C / |Inert atmosphere 3: dichloromethane / 11 h / 20 °C / |Inert atmosphere 4: copper(l) iodide; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran / 4 h / 0 °C / |Inert atmosphere View Scheme

1: 84 percent / NaBH4 / methanol / 0.33 h / Ambient temperature 2: 74 percent / PPh3*Br2 / acetonitrile 3: 1.) Na / 1.)diglyme 2.) diglyme 140 deg C, 2h 4: 40percent aq NaOH / H2O; ethanol / 4 h / Ambient temperature 5: 1.5 M HCl / bis-(2-methoxy-ethyl) ether / 1 h / 120 °C View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / diethyl ether / 0.5 h / 20 °C / |Inert atmosphere 2: copper(l) iodide; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.25 h / -20 - 0 °C / |Inert atmosphere 3: dichloromethane / 11 h / 20 °C / |Inert atmosphere 4: copper(l) iodide; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran / 4 h / 0 °C / |Inert atmosphere 5: lithium hydroxide hydrate / water; methanol / 1.5 h / 60 °C / |Inert atmosphere View Scheme

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / diethyl ether / 0.5 h / 20 °C / |Inert atmosphere 2: copper(l) iodide; N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.25 h / -20 - 0 °C / |Inert atmosphere 3: sodium dihydrogen phosphate dihydrate; sodium chlorite; 2-methyl-but-2-ene / water; acetonitrile / 1.5 h / 20 °C / |Inert atmosphere View Scheme

jones reagent in acetone T=-70°C;