triethylamine in N,N-dimethyl-formamide 4 h; Heating;

1: propionic acid / H2O; acetonitrile / 2 h / 60 °C 2: acetic acid; aq. H2O2 / 3 h / 20 °C View Scheme

1.1: [bis(triphenyl-λ5-phosphanylidene)ammonium][Cl] / 1,2-dichloro-benzene / 3 h / 180 °C 1.2: -30 - 0 °C / pH 8.5 2.1: hydrogenchloride / acetone / 40 °C 3.1: potassium carbonate / acetonitrile / 14 h / 40 °C 4.1: tetrahydrofuran / 0.17 h / 20 °C 5.1: boron trifluoride diethyl etherate / benzene / 2 h / 20 °C / |Inert atmosphere 6.1: sulfuric acid / 24 h / 0 °C / |Reflux 7.1: ethyl mercaptan sodium salt / N,N-dimethyl-formamide / |Reflux 8.1: sodium nitrite; nitric acid / water / 0.5 h 8.2: |Heating 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.75 h / |Inert atmosphere View Scheme

1.1: potassium carbonate / acetonitrile / 14 h / 40 °C 2.1: tetrahydrofuran / 0.17 h / 20 °C 3.1: boron trifluoride diethyl etherate / benzene / 2 h / 20 °C / |Inert atmosphere 4.1: sulfuric acid / 24 h / 0 °C / |Reflux 5.1: ethyl mercaptan sodium salt / N,N-dimethyl-formamide / |Reflux 6.1: sodium nitrite; nitric acid / water / 0.5 h 6.2: |Heating 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2.75 h / |Inert atmosphere View Scheme

1.1: NaNO2; HNO3 / H2O / 0.17 h 1.2: 98 percent / Na2CO3 / H2O / Heating 2.1: 89 percent / LiAlH4 / tetrahydrofuran View Scheme

1.1: 92 percent / Ac2O / H2O / 1 h / 100 °C 2.1: 88 percent / MeONa / toluene / 24 h 3.1: 83 percent / aq. HCl / methanol / 20 h / 20 °C 4.1: NaNO2; HNO3 / H2O / 0.17 h 4.2: 98 percent / Na2CO3 / H2O / Heating 5.1: 89 percent / LiAlH4 / tetrahydrofuran View Scheme

1.1: 88 percent / MeONa / toluene / 24 h 2.1: 83 percent / aq. HCl / methanol / 20 h / 20 °C 3.1: NaNO2; HNO3 / H2O / 0.17 h 3.2: 98 percent / Na2CO3 / H2O / Heating 4.1: 89 percent / LiAlH4 / tetrahydrofuran View Scheme

1: t-BuOK / methanol / 4 h 2: 85 percent / NaIO4, K2S2O2(OH)4 / dioxane; H2O / 24 h / 60 °C 3: 99 percent / LiAlH4 / tetrahydrofuran / 0.25 h View Scheme

1: 85 percent / NaIO4, K2S2O2(OH)4 / dioxane; H2O / 24 h / 60 °C 2: 99 percent / LiAlH4 / tetrahydrofuran / 0.25 h View Scheme

manganese(IV) oxide in 1,4-dioxane T=80°C; 6 h;