thionyl chloride

1.1: pyridine; piperidine 1.2: HCl / Heating 2.1: thionyl chloride / 20 °C View Scheme

N-ethyl-N,N-diisopropylamine in acetonitrile T=150°C; 1.5 h; Microwave irradiation;

1: NaN3 / H2O / 5 h / 0 °C 2: toluene / 110 °C 3: 80 °C 4: 99 percent / Et3SiH / trifluoroacetic acid / 0.5 h / -10 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 1.2: 2.5 h / -78 - 0 °C 2.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.17 h / -40 °C / |Inert atmosphere 2.2: 0.17 h / -40 °C 2.3: 2 h / -40 - 20 °C 3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / |Inert atmosphere 3.2: 1.5 h / -78 - -50 °C 4.1: dihydrogen peroxide; lithium hydroxide hydrate / tetrahydrofuran; water / 4 h / 20 °C / |Cooling with ice 5.1: oxalyl dichloride / dichloromethane / 1 h / 20 °C 6.1: triethylamine / dichloromethane / 1 h / 20 °C / |Cooling with ice 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / |Cooling with ice View Scheme

1: sodium tetrahydroborate; water; sodium carbonate / acetonitrile / 0.5 h / 5 - 13 °C 2: anhydrous xylene / 16 h / 120 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 16.67 h / 0 - 48 °C 4: water; acetone / 55 - 58 °C 5: sodium hydroxide / dichloromethane; water 6: hydrogen; 5 palladium on charcoal / ethanol / 22 h / 24 °C / 3750.38 Torr 7: dl-methionine; methanesulfonic acid / 16 h / 80 °C View Scheme