lithium triethylborohydride in tetrahydrofuran T=65°C; 3 h;

1: 100 percent / diethyl ether 2: 85 percent / sulfur tetrafluoride 3: 90 percent / potassium hydroxide / H2O; ethanol 4: 75 percent / borane-methyl sulfide 5: 90 percent 6: lithium triethylborohydride / tetrahydrofuran / 3 h / 65 °C View Scheme

1: 81 percent / hydrobromic acid, acetic anhydride / 24 h / Heating 2: 100 percent / diethyl ether 3: 85 percent / sulfur tetrafluoride 4: 90 percent / potassium hydroxide / H2O; ethanol 5: 75 percent / borane-methyl sulfide 6: 90 percent 7: lithium triethylborohydride / tetrahydrofuran / 3 h / 65 °C View Scheme

1: 60 percent / potassium hydroxide / H2O / 48 h / Heating 2: 81 percent / hydrobromic acid, acetic anhydride / 24 h / Heating 3: 100 percent / diethyl ether 4: 85 percent / sulfur tetrafluoride 5: 90 percent / potassium hydroxide / H2O; ethanol 6: 75 percent / borane-methyl sulfide 7: 90 percent 8: lithium triethylborohydride / tetrahydrofuran / 3 h / 65 °C View Scheme

1: 90 percent 2: lithium triethylborohydride / tetrahydrofuran / 3 h / 65 °C View Scheme

1: 85 percent / sulfur tetrafluoride 2: 90 percent / potassium hydroxide / H2O; ethanol 3: 75 percent / borane-methyl sulfide 4: 90 percent 5: lithium triethylborohydride / tetrahydrofuran / 3 h / 65 °C View Scheme

1: 75 percent / borane-methyl sulfide 2: 90 percent 3: lithium triethylborohydride / tetrahydrofuran / 3 h / 65 °C View Scheme