n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane; water; ethyl acetate

1: 61 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 1) -78 deg C, 2) 25 deg C 2: 1) n-butyllithium / 1) a) THF, -78 deg C, 1h, b) -5 deg C 5 min, 2) HMPA, room temperature View Scheme

1: 99 percent / H2, quinoline / Pd/BaSO4 / methanol / 762 Torr / Ambient temperature 2: 83 percent / Dowex / methanol / 45 °C View Scheme