in acetic acid

lithium hydroxide in tetrahydrofuran; water T=50°C;

sodium hydroxide in 1,4-dioxane

1: 82 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 2.5 h / Ambient temperature 2: 79 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.25 h / -78 °C 3: 53 percent / lithiumhydroxyde / tetrahydrofuran; H2O / 24 h / 50 °C View Scheme

1: 82 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 2.5 h / Ambient temperature 2: 79 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.25 h / -78 °C 3: 53 percent / lithiumhydroxyde / tetrahydrofuran; H2O / 24 h / 50 °C View Scheme

1: 83 percent / ethanol / 0.5 h / Ambient temperature 2: 78 percent / TMEDA, n-butyllithium / tetrahydrofuran; hexane / from -78 to room temperature, 17 h 3: 82 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 2.5 h / Ambient temperature 4: 79 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.25 h / -78 °C 5: 53 percent / lithiumhydroxyde / tetrahydrofuran; H2O / 24 h / 50 °C View Scheme

1: 86 percent / ozone / CH2Cl2 / -78 °C 2: 83 percent / ethanol / 0.5 h / Ambient temperature 3: 78 percent / TMEDA, n-butyllithium / tetrahydrofuran; hexane / from -78 to room temperature, 17 h 4: 82 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 2.5 h / Ambient temperature 5: 79 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.25 h / -78 °C 6: 53 percent / lithiumhydroxyde / tetrahydrofuran; H2O / 24 h / 50 °C View Scheme

1: 79 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.25 h / -78 °C 2: 53 percent / lithiumhydroxyde / tetrahydrofuran; H2O / 24 h / 50 °C View Scheme

1: 87 percent / formic acid / 18 h / Ambient temperature 2: 86 percent / ozone / CH2Cl2 / -78 °C 3: 83 percent / ethanol / 0.5 h / Ambient temperature 4: 78 percent / TMEDA, n-butyllithium / tetrahydrofuran; hexane / from -78 to room temperature, 17 h 5: 82 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 2.5 h / Ambient temperature 6: 79 percent / m-chloroperbenzoic acid / CH2Cl2 / 1.25 h / -78 °C 7: 53 percent / lithiumhydroxyde / tetrahydrofuran; H2O / 24 h / 50 °C View Scheme

1: 1.) n-butyllithium / 1.) THF/TMEDA 1:1, 2.) RT, 17 h 2: 82 percent / DMAP / triethylamine 3: 79 percent / mCPBA / CH2Cl2 / -78 °C 4: 53 percent / LiOH / H2O; tetrahydrofuran / 50 °C View Scheme