1: 55 percent / CsF / dimethylformamide / 3 h / Heating 2: 97 percent / 20percent aq. KOH / methanol / 3 h / Heating 3: SOCl2 / CH2Cl2 / 3 h / Heating View Scheme

1.1: pyridinium p-tosylate / CH2Cl2 / 1 h 2.1: 85 percent / KHMDS; 2-sulfonyloxaziridine / tetrahydrofuran; toluene / 0.33 h / -78 °C 3.1: 91 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 20 °C 4.1: 93 percent / DIBALH / toluene; CH2Cl2 / 2 h / -78 °C 5.1: pyridinium p-tosylate / methanol / 4 h / 20 °C 5.2: 50 percent / 3M HCl / tetrahydrofuran; H2O / 3 h / 20 °C View Scheme

1: With sodium tetrahydroborate in water T=0 - 24.5°C; 8.16667 h; 2: With hydrogenchloride; water T=0 - 5°C; 0.25 h; Product distribution / selectivity;

potassium carbonate in acetone

ammonium hydroxide

1: pyridinium p-tosylate / CH2Cl2 / 1 h 2: 52 percent / DIBALH / toluene / 0.5 h / -78 °C 3: 50 percent / Amberlite-H+ / H2O; tetrahydrofuran / 4 h View Scheme

toluene-4-sulfonic acid in chloroform 8 h; RefluxDarknessInert atmosphere;