hydrogenchloride in tetrahydrofuran Ambient temperature;

1: 1) n-butyllithium / 1) tetrahydrofuran, -70 deg C, 1h, 2) tetrahydrofuran up to 0 deg C 2: 42 percent / 20 h / 95 °C 3: 53 percent / sodium hydride / paraffin; dimethylformamide / 13 h / 80 °C 4: 89 percent / aq. hydrochloric acid / tetrahydrofuran / Ambient temperature View Scheme

1: 42 percent / 20 h / 95 °C 2: 53 percent / sodium hydride / paraffin; dimethylformamide / 13 h / 80 °C 3: 89 percent / aq. hydrochloric acid / tetrahydrofuran / Ambient temperature View Scheme

1: 53 percent / sodium hydride / paraffin; dimethylformamide / 13 h / 80 °C 2: 89 percent / aq. hydrochloric acid / tetrahydrofuran / Ambient temperature View Scheme

1: Ambient temperature 2: 1) sodium hydride / 1) mineral oil, tetrahydrofuran, 50 deg C, 2) tetrahydrofuran, 50 deg C, overnight View Scheme

sodium hydride 1) mineral oil, tetrahydrofuran, 50 deg C, 2) tetrahydrofuran, 50 deg C, overnight; Yield given. Multistep reaction. Yields of byproduct given;