hydrogenchloride; hydrogen; platinum(IV) oxide in ethanol; water P=2508.23 Torr; 24 h; Heating / reflux;

1: diethyl ether 2: PhSH, Py / acetone 3: H2 / PtO2 / ethanol 4: aq. KOH View Scheme

1: H2 / PtO2 / ethanol 2: aq. KOH View Scheme

1: PhSH, Py / acetone 2: H2 / PtO2 / ethanol 3: aq. KOH View Scheme

1.1: LDA / tetrahydrofuran / 2.5 h / 0 °C 1.2: 66 percent / tetrahydrofuran / 16 h / -100 - 20 °C / pH 7 2.1: CeCl3 / tetrahydrofuran / 2 h / -78 °C 2.2: tetrahydrofuran / 2.5 h / -105 - -50 °C 3.1: BH3 / tetrahydrofuran / 4 h / Heating 4.1: 1.02 g / K2CO3 / CH2Cl2 / 14 h 5.1: aq. LiBF4 / acetonitrile / Heating 6.1: 616 mg / PPh3; diisopropyl azodiacarboxylate / tetrahydrofuran / 24 h / 20 °C 7.1: aq. H5IO6 / RuCl3 / acetonitrile; CCl4 / 20 °C 8.1: sodium; naphthalene / 1,2-dimethoxy-ethane / 0.5 h / -78 °C View Scheme

potassium hydroxide