1: 2-fluoro-pyridine With lithium diisopropyl amide in tetrahydrofuran T=-75°C; 4 h; 2: ethyl-α,α,α-trifluoroacetate T=-78 - -45°C; 3: nitromethane T=20°C; Alkaline conditions;

1.1: lithium diisopropylamide / tetrahydrofuran / 1.5 h / -75 °C 1.2: tetrahydrofuran 2.1: 290 g / potassium carbonate / tetrahydrofuran / 20 °C View Scheme

potassium carbonate in tetrahydrofuran T=20°C; Henry reaction;

hydrogen; nickel in ethanol T=20°C;

1: 81 percent / H2 / Raney-nickel / ethanol / 20 °C 2: 83 percent / thionyl chloride; pyridine / CH2Cl2 / 20 °C View Scheme

1: 81 percent / H2 / Raney-nickel / ethanol / 20 °C 2: 83 percent / thionyl chloride; pyridine / CH2Cl2 / 20 °C 3: 79 percent / m-chloroperbenzoic acid / ethyl acetate / 1 h / 0 °C View Scheme

1: 81 percent / H2 / Raney-nickel / ethanol / 20 °C 2: 83 percent / thionyl chloride; pyridine / CH2Cl2 / 20 °C 3: 79 percent / m-chloroperbenzoic acid / ethyl acetate / 1 h / 0 °C 4: 76 percent / aq. nitric acid / trifluoroacetic acid / 2 h / 70 °C View Scheme

1: 81 percent / H2 / Raney-nickel / ethanol / 20 °C 2: 83 percent / thionyl chloride; pyridine / CH2Cl2 / 20 °C 3: 79 percent / m-chloroperbenzoic acid / ethyl acetate / 1 h / 0 °C 4: 76 percent / aq. nitric acid / trifluoroacetic acid / 2 h / 70 °C 5: 100 percent / hexamethyldisilazane; trichloroacetyl chloride / tetrahydrofuran / 0 - 20 °C View Scheme

1: 81 percent / H2 / Raney-nickel / ethanol / 20 °C 2: 83 percent / thionyl chloride; pyridine / CH2Cl2 / 20 °C 3: 79 percent / m-chloroperbenzoic acid / ethyl acetate / 1 h / 0 °C 4: 76 percent / aq. nitric acid / trifluoroacetic acid / 2 h / 70 °C 5: 100 percent / hexamethyldisilazane; trichloroacetyl chloride / tetrahydrofuran / 0 - 20 °C 6: 65 percent / sodium hydride / dimethylformamide; various solvent(s) / 0.75 h / 20 °C View Scheme