sodium tetrahydroborate in ethanol

1: potassium tert-butylate / dimethyl sulfoxide / 0.17 h / 20 °C 2: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 0 - 20 °C 3: water / tetrahydrofuran / 2 h / 50 °C View Scheme

1.1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C / |Schlenk technique 2.1: potassium tert-butylate / tetrahydrofuran / 0 °C / |Schlenk technique 3.1: hydrogenchloride / tetrahydrofuran; water / |Schlenk technique; |Reflux 4.1: sodium tetrahydroborate / methanol / 0 - 20 °C / |Schlenk technique 5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / |Schlenk technique 6.1: sodium hydride / mineral oil; tetrahydrofuran / |Inert atmosphere; |Schlenk technique; |Reflux 7.1: palladium 10 on activated carbon; hydrogen / ethanol / 20 °C / 3040.2 Torr / |Schlenk technique 8.1: triethylamine; Methanesulfonyl azide / acetonitrile / 20 °C / |Schlenk technique 9.1: [Cu(I)(CH3CN)4]PF6; Na[B(3,5-(CF3)2C6H3)4]; C35H30N2O2 / dichloromethane / 0.08 h / 25 °C / |Inert atmosphere; |Schlenk technique; |Glovebox 10.1: sodium hydroxide / methanol; tetrahydrofuran; water / 6 h / 0 - 20 °C / |Schlenk technique 10.2: |Schlenk technique View Scheme

N-bromosuccinmide in DMF (N,N-dimethyl-formamide) T=20°C; 5 h;

potassium carbonate in acetonitrile 3 h; Heating / reflux;

morpholine in toluene 15 h; Heating;

sulfuric acid; potassium carbonate in butanone

1: K2CO3 / butan-2-one / 4 h / Heating 2: KOH / ethanol / 0.75 h / Heating View Scheme

1: With 1,4-diaza-bicyclo[2.2.2]octane Heating; 2: With 1 Pd/C; hydrogen

potassium tert-butylate in dimethyl sulfoxide T=20°C; 0.166667 h;