lithium diisopropyl amide in tetrahydrofuran T=-15°C; Ramberg-Backlund rearrangement; 0.5 h;

tri[2-(2-methoxyethoxy)ethyl]amine; sodium hydride in tetrahydrofuran T=62°C; 2.5 h;

in toluene T=50°C;

(i) NaH, (ii) /BRN= 605842/; Multistep reaction;

in tetrahydrofuran T=45°C; 50 h; Yield given;

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -10 - 20 °C 1.2: 80 percent / tetrahydrofuran; hexane / 20 h / 0 - 20 °C 2.1: 66 percent / CCl4; NaOH / dimethylformamide / 1 h / 0 °C 3.1: 90 percent / lithium diisopropylamide / tetrahydrofuran / 0.5 h / -15 °C View Scheme

1: 66 percent / CCl4; NaOH / dimethylformamide / 1 h / 0 °C 2: 90 percent / lithium diisopropylamide / tetrahydrofuran / 0.5 h / -15 °C View Scheme

potassium hydride 1.) THF, reflux, 10 min 2.) DMSO, 90-95 deg C; Yield given. Multistep reaction;