1: 100 percent / diethyl ether 2: 85 percent / sulfur tetrafluoride 3: 90 percent / potassium hydroxide / H2O; ethanol 4: 68 percent View Scheme

1: 100 percent / diethyl ether 2: 85 percent / sulfur tetrafluoride 3: 90 percent / potassium hydroxide / H2O; ethanol 4: 72 percent / tert-butyl hypoiodite / Irradiation 5: 38 percent / 96 h / Irradiation View Scheme

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

<b>Multi-step reaction with 2 steps<br /> </b>1.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / methanol / 10 h / 1551.49 Torr<br />2.1: sodium nitrite; acetic acid / water / 65 &deg;C<br />2.2: 5 h / 65 &deg;C<br />2.3: pH 3<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 60 percent / potassium hydroxide / H₂O / 48 h / Heating<br />2: 81 percent / hydrobromic acid, acetic anhydride / 24 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1.1: sodium periodate; ruthenium trichloride / ethyl acetate; acetonitrile; water / 5 - 39 &deg;C / Industry scale<br />2.1: sulfuric acid / 16 h / 7 - 12 &deg;C / Reflux<br />3.1: N,N,N',N',N'',N''-hexamethylphosphoric triamide; diisopropylamine; n-butyllithium / tetrahydrofuran; hexanes / 2 h / -73 - -10 &deg;C / Inert atmosphere<br />3.2: 16 h / -70 - 20 &deg;C<br />4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 16 h / 15 - 20 &deg;C<br />4.2: 10 &deg;C / pH ~ 4<br />5.1: N-ethyl-N,N-diisopropylamine; diphenyl phosphoryl azide / toluene / 2 h / 10 - 110 &deg;C<br />5.2: 40 h / 110 &deg;C<br />6.1: hydrogenchloride; hydrogen / palladium 10 on activated carbon / methanol / 10 h / 1551.49 Torr<br />7.1: sodium nitrite; acetic acid / water / 65 &deg;C<br />7.2: 5 h / 65 &deg;C<br />7.3: pH 3<br /> <br /> &nbsp;