1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 45 min; 2.) THF, -78 deg C to RT 2: 96 percent / lithium aluminium hydride / various solvent(s) / Heating 3: 97 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -78 °C View Scheme

1: 96 percent / lithium aluminium hydride / various solvent(s) / Heating 2: 97 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.25 h / -78 °C View Scheme

1.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C 2.2: 18 h / -78 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - 20 °C 1.2: 18 h / -78 - 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h View Scheme

1: hydrogenchloride / water; methanol / 0.5 h / 23 °C / |Inert atmosphere 2: triethylamine; oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.67 h / -78 - 23 °C / |Inert atmosphere View Scheme

1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium hydrogencarbonate; potassium bromide; NaClO / dichloromethane; water / 0.25 h / 0 °C / |Inert atmosphere 2: n-butyllithium / tetrahydrofuran / 1.5 h / 0 - 23 °C / |Inert atmosphere 3: hydrogenchloride / water; methanol / 0.5 h / 23 °C / |Inert atmosphere 4: triethylamine; oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.67 h / -78 - 23 °C / |Inert atmosphere View Scheme

1: n-butyllithium / tetrahydrofuran / 1.5 h / 0 - 23 °C / |Inert atmosphere 2: hydrogenchloride / water; methanol / 0.5 h / 23 °C / |Inert atmosphere 3: triethylamine; oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 0.67 h / -78 - 23 °C / |Inert atmosphere View Scheme

T=450 - 500°C;

Yield given. Multistep reaction;