hydrogen in methanol T=20°C; P=3102.97 Torr; 3 h;

1: 98 percent / H2SO4 2: 72 percent / NaOMe / dioxane / 45 h / 110 °C 3: 73 percent / water / aq. NaOH / dioxane / 18 h / 110 °C 4: 83 percent / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 5: 58 percent / BF3*MeOH / 17 h / Ambient temperature 6: BBr3 / CH2Cl2 / 18 h / -78 °C 7: 40 percent / Fremy's salt, KH2PO4 / H2O; acetone / 0.5 h / Ambient temperature View Scheme

1: 72 percent / NaOMe / dioxane / 45 h / 110 °C 2: 73 percent / water / aq. NaOH / dioxane / 18 h / 110 °C 3: 83 percent / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 4: 58 percent / BF3*MeOH / 17 h / Ambient temperature 5: BBr3 / CH2Cl2 / 18 h / -78 °C 6: 40 percent / Fremy's salt, KH2PO4 / H2O; acetone / 0.5 h / Ambient temperature View Scheme

1: 73 percent / water / aq. NaOH / dioxane / 18 h / 110 °C 2: 83 percent / PCC, NaOAc / CH2Cl2 / 2.5 h / Ambient temperature 3: 58 percent / BF3*MeOH / 17 h / Ambient temperature 4: BBr3 / CH2Cl2 / 18 h / -78 °C 5: 40 percent / Fremy's salt, KH2PO4 / H2O; acetone / 0.5 h / Ambient temperature View Scheme

in methanol 0.5 h; Irradiation;

1: 46 percent / Na, naphthalene / tetrahydrofuran / 1 h / -30 °C 2: 80 percent / Fremy's salt, KH2PO4 / H2O; acetone / 0.42 h View Scheme

1: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, RT, 2 h 2: 1.) lithium cyclohexylisopropylamide / 1.) THF, hexane, from -23 to -20 deg C, 5 h, 2.) THF, hexane, a.) from -23 to -19 deg C, 2 h, b.) RT, overnight 3: 1.) lithium cyclohexylisopropylamide, HMPA / 1.) THF, hexane, from -23 to -19, 5 h, 2.) THF, hexane, a.) from -23 to -14, 2 h, b.) RT, overnight 4: 89 percent / Et3N / CHCl3 / 1 h / Ambient temperature 5: 82 percent / AlCl3, anisole / 0.17 h / 0 °C 6: 81 percent / aq HCl / methanol / 4 h / Heating 7: 84 percent / Fremy's salt, KH2PO4 / H2O; acetone / 0.17 h / Ambient temperature View Scheme

1: 1.) lithium cyclohexylisopropylamide / 1.) THF, hexane, from -23 to -20 deg C, 5 h, 2.) THF, hexane, a.) from -23 to -19 deg C, 2 h, b.) RT, overnight 2: 1.) lithium cyclohexylisopropylamide, HMPA / 1.) THF, hexane, from -23 to -19, 5 h, 2.) THF, hexane, a.) from -23 to -14, 2 h, b.) RT, overnight 3: 89 percent / Et3N / CHCl3 / 1 h / Ambient temperature 4: 82 percent / AlCl3, anisole / 0.17 h / 0 °C 5: 81 percent / aq HCl / methanol / 4 h / Heating 6: 84 percent / Fremy's salt, KH2PO4 / H2O; acetone / 0.17 h / Ambient temperature View Scheme

1: 1.) lithium cyclohexylisopropylamide, HMPA / 1.) THF, hexane, from -23 to -19, 5 h, 2.) THF, hexane, a.) from -23 to -14, 2 h, b.) RT, overnight 2: 89 percent / Et3N / CHCl3 / 1 h / Ambient temperature 3: 82 percent / AlCl3, anisole / 0.17 h / 0 °C 4: 81 percent / aq HCl / methanol / 4 h / Heating 5: 84 percent / Fremy's salt, KH2PO4 / H2O; acetone / 0.17 h / Ambient temperature View Scheme

1.1: trichlorophosphate / 10 - 20 °C / Inert atmosphere 1.2: 20 - 35 °C / Inert atmosphere 1.3: 20 - 30 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / methanol / 5 h / 20 °C / Inert atmosphere 3.1: sodium cyanoborohydride / methanol / 2 h / 20 °C / Inert atmosphere 4.1: [bis(acetoxy)iodo]benzene; acetic acid; trifluoroacetic acid / methanol; water / 1 h / 50 °C / Inert atmosphere View Scheme