triethylamine hydrofluoric acid in tetrahydrofuran 2 h; Ambient temperature;

1: 95 percent / imidazole / dimethylformamide / Ambient temperature 2: 1.) n-BuLi, i-Pr2NH / 1.) THF, -76 deg C, 0.5 h, 2.) THF, -76 deg C, 1 h 3: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 4: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 1.) n-BuLi, i-Pr2NH / 1.) THF, -76 deg C, 0.5 h, 2.) THF, -76 deg C, 1 h 2: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 3: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 2: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 88 percent / AcOH, BF3*Et2O / 5 °C 2: 95 percent / imidazole / dimethylformamide / Ambient temperature 3: 1.) n-BuLi, i-Pr2NH / 1.) THF, -76 deg C, 0.5 h, 2.) THF, -76 deg C, 1 h 4: 48 percent / 1percent NaOH, Raney nickel W-2 / tetrahydrofuran / 5 h / Heating 5: 73 percent / 1.3M Et3N*HF / tetrahydrofuran / 2 h / Ambient temperature View Scheme

hydrogenchloride

diethyl ether