hydrogen; palladium on activated charcoal in ethanol

1: 2-Nitropropane With sodium hydride in methanol T=0°C; 2: N-(2-methylnaphthalene)-2,4,6-triphenylpyridinium tetrafluoroborate in dimethyl sulfoxide T=70°C;

1.1: lithium aluminium tetrahydride / diethyl ether / 5 h / 20 °C / |Inert atmosphere; |Cooling with ice 2.1: ethanol / |Inert atmosphere; |Reflux 3.1: sodium methylate / toluene / 0.33 h / |Inert atmosphere 3.2: 13 h / 60 °C / |Inert atmosphere View Scheme

1.1: triethylamine / ethanol / 20 °C 2.1: sodium hydride / various solvent(s); methanol / 0 °C 2.2: dimethylsulfoxide / 70 °C View Scheme