1: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, 0 deg C, 2.) 45 min, room temperature 2: 73 percent / 1 N NaOH / tetrahydrofuran / 1.5 h / Ambient temperature View Scheme

sodium ethanolate in tetrahydrofuran; ethanol 1 h; Ambient temperature; Product distribution;

1: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, 0 deg C, 2.) 45 min, room temperature 2: 78 percent / 1 N NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 3: 85 percent / Et3N / benzene / 1 h / Heating 4: 1.) LDA, HMPA, 2.) HMPA / 1.) THF, hexane, 0 deg C, 2.) THF, 1 h, room temperature 5: 1 N sodium ethoxide / ethanol; tetrahydrofuran / 4 h / Ambient temperature 6: water, AcOH / tetrahydrofuran / Ambient temperature View Scheme

1: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, 0 deg C, 2.) 45 min, room temperature 2: 78 percent / 1 N NaOH / tetrahydrofuran / 1.5 h / Ambient temperature 3: 85 percent / Et3N / benzene / 1 h / Heating 4: 1.) LDA, HMPA, 2.) HMPA / 1.) THF, hexane, 0 deg C, 2.) THF, 1 h, room temperature View Scheme

lithium diisopropyl amide in tetrahydrofuran; hexane 0.333333 h; Ambient temperature;

n-butyllithium; diisopropylamine 1.) THF, hexane, 0 deg C, 2.) 45 min, room temperature; Yield given. Multistep reaction. Yields of byproduct given;

n-butyllithium 1.) THF, hexane, 0 deg C, 2.) THF, room temperature, overnight; Yield given. Multistep reaction. Yields of byproduct given;

sodium ethanolate in tetrahydrofuran; ethanol 1 h; Ambient temperature; Product distribution;

n-butyllithium; diisopropylamine multistep reaction, amide exchange reaction; other carboxamides, other N1-acyl-N1,N2-di(p-nitrophenyl)formamidines; Product distribution;