sodium hydroxide in tetrahydrofuran; water

1.1: NaBH4; isobutyric acid / toluene / 3 h / 0 °C 1.2: HBr / ethyl acetate; propionic acid / 0 °C 1.3: aq. NaHCO3 2.1: Na / ethanol / 15 h / 80 °C 3.1: HCl / ethyl acetate; dioxane / 0 - 20 °C 4.1: LiOH*H2O / tetrahydrofuran; ethanol; H2O / 36 h / 0 °C 5.1: HCO2NH4 / Pd/C / methanol / 2 h / Heating 6.1: NaHCO3 / acetone; H2O / 0 - 20 °C View Scheme

1.1: p-TsOH / benzene / 4 h / Heating 2.1: NaBH4; isobutyric acid / toluene / 3 h / 0 °C 2.2: HBr / ethyl acetate; propionic acid / 0 °C 2.3: aq. NaHCO3 3.1: Na / ethanol / 15 h / 80 °C 4.1: HCl / ethyl acetate; dioxane / 0 - 20 °C 5.1: LiOH*H2O / tetrahydrofuran; ethanol; H2O / 36 h / 0 °C 6.1: HCO2NH4 / Pd/C / methanol / 2 h / Heating 7.1: NaHCO3 / acetone; H2O / 0 - 20 °C View Scheme

1: Na / ethanol / 15 h / 80 °C 2: HCl / ethyl acetate; dioxane / 0 - 20 °C 3: LiOH*H2O / tetrahydrofuran; ethanol; H2O / 36 h / 0 °C 4: HCO2NH4 / Pd/C / methanol / 2 h / Heating 5: NaHCO3 / acetone; H2O / 0 - 20 °C View Scheme

sodium hydrogencarbonate in water; acetone T=0 - 20°C;

1.1: acetyl chloride / Heating 1.2: NH3 gas / CH2Cl2 / 20 °C 1.3: 74 percent / phenyliodine(III) trifluoroacetate / acetonitrile; H2O / 20 °C 2.1: 81 percent / sodium hydroxide / tetrahydrofuran; H2O View Scheme

1.1: phenyliodine(III) bis(trifluoroacetate) / acetonitrile; H2O / 20 °C 1.2: 77 percent / cc. HCl 2.1: 81 percent / sodium hydroxide / tetrahydrofuran; H2O View Scheme