sodium hydride in tetrahydrofuran T=60°C; 4 h;

1: 100 percent / potassium carbonate / acetone / 4 h / Heating 2: 91 percent / sulfuric acid / methanol / 3 h / Heating 3: 70 percent / n-butyllithium / tetrahydrofuran; hexane / 48 h / Ambient temperature 4: 1.) borane-methyl sulfide complex, 2.) hydrogen peroxide, sodium hydroxide / 1.) THF, room temperature, 3 h, 2.) water, 25 deg C; reflux, 1 h 6: sodium iodide / acetone / Heating 7: 60 percent / hydrochloric acid, glacial acetic acid / H2O / 0.5 h / 70 °C 8: sodium hydride / tetrahydrofuran / 4 h / 60 °C View Scheme

1: 1.) borane-methyl sulfide complex, 2.) hydrogen peroxide, sodium hydroxide / 1.) THF, room temperature, 3 h, 2.) water, 25 deg C; reflux, 1 h 3: sodium iodide / acetone / Heating 4: 60 percent / hydrochloric acid, glacial acetic acid / H2O / 0.5 h / 70 °C 5: sodium hydride / tetrahydrofuran / 4 h / 60 °C View Scheme

1: 91 percent / sulfuric acid / methanol / 3 h / Heating 2: 70 percent / n-butyllithium / tetrahydrofuran; hexane / 48 h / Ambient temperature 3: 1.) borane-methyl sulfide complex, 2.) hydrogen peroxide, sodium hydroxide / 1.) THF, room temperature, 3 h, 2.) water, 25 deg C; reflux, 1 h 5: sodium iodide / acetone / Heating 6: 60 percent / hydrochloric acid, glacial acetic acid / H2O / 0.5 h / 70 °C 7: sodium hydride / tetrahydrofuran / 4 h / 60 °C View Scheme

1: 60 percent / hydrochloric acid, glacial acetic acid / H2O / 0.5 h / 70 °C 2: sodium hydride / tetrahydrofuran / 4 h / 60 °C View Scheme

2: sodium iodide / acetone / Heating 3: 60 percent / hydrochloric acid, glacial acetic acid / H2O / 0.5 h / 70 °C 4: sodium hydride / tetrahydrofuran / 4 h / 60 °C View Scheme

1: sodium iodide / acetone / Heating 2: 60 percent / hydrochloric acid, glacial acetic acid / H2O / 0.5 h / 70 °C 3: sodium hydride / tetrahydrofuran / 4 h / 60 °C View Scheme

1: 70 percent / n-butyllithium / tetrahydrofuran; hexane / 48 h / Ambient temperature 2: 1.) borane-methyl sulfide complex, 2.) hydrogen peroxide, sodium hydroxide / 1.) THF, room temperature, 3 h, 2.) water, 25 deg C; reflux, 1 h 4: sodium iodide / acetone / Heating 5: 60 percent / hydrochloric acid, glacial acetic acid / H2O / 0.5 h / 70 °C 6: sodium hydride / tetrahydrofuran / 4 h / 60 °C View Scheme