diisobutylaluminium hydride in tetrahydrofuran; hexane T=-78°C; 4 h;

1: 18 percent / diisobutylaluminum hydride (DIBAH) / tetrahydrofuran; hexane / 4 h / -78 °C 2: 97 percent / pyridinium tosylate / CH2Cl2 / 24 h / Ambient temperature 3: 99 percent / 10percent aq. NaOH / methanol / 0.67 h / Ambient temperature View Scheme

1: 18 percent / diisobutylaluminum hydride (DIBAH) / tetrahydrofuran; hexane / 4 h / -78 °C 2: 97 percent / pyridinium tosylate / CH2Cl2 / 24 h / Ambient temperature 3: 99 percent / 10percent aq. NaOH / methanol / 0.67 h / Ambient temperature 4: 98 percent / triethylamine / CH2Cl2 / 17 h / 0 °C 5: 88 percent / triethylamine / CH2Cl2 / 12 h / Ambient temperature 6: 54 percent / pyridinium tosylate / aq. ethanol / 24 h / 50 °C View Scheme

1: 18 percent / diisobutylaluminum hydride (DIBAH) / tetrahydrofuran; hexane / 4 h / -78 °C 2: 97 percent / pyridinium tosylate / CH2Cl2 / 24 h / Ambient temperature 3: 99 percent / 10percent aq. NaOH / methanol / 0.67 h / Ambient temperature 4: 76 percent / triethylamine / CH2Cl2 / 24 h / Ambient temperature 5: 76 percent / pyridinium tosylate / aq. ethanol / 24 h / 50 °C View Scheme

1: 18 percent / diisobutylaluminum hydride (DIBAH) / tetrahydrofuran; hexane / 4 h / -78 °C 2: 97 percent / pyridinium tosylate / CH2Cl2 / 24 h / Ambient temperature 3: 99 percent / 10percent aq. NaOH / methanol / 0.67 h / Ambient temperature 4: 98 percent / triethylamine / CH2Cl2 / 17 h / 0 °C 5: 88 percent / triethylamine / CH2Cl2 / 12 h / Ambient temperature 6: 54 percent / pyridinium tosylate / aq. ethanol / 24 h / 50 °C 7: 78 percent / Me2SO, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C View Scheme

1: 18 percent / diisobutylaluminum hydride (DIBAH) / tetrahydrofuran; hexane / 4 h / -78 °C 2: 97 percent / pyridinium tosylate / CH2Cl2 / 24 h / Ambient temperature 3: 99 percent / 10percent aq. NaOH / methanol / 0.67 h / Ambient temperature 4: 76 percent / triethylamine / CH2Cl2 / 24 h / Ambient temperature 5: 76 percent / pyridinium tosylate / aq. ethanol / 24 h / 50 °C 6: 77 percent / Me2SO, trifluoroacetic anhydride / CH2Cl2 / 0.5 h / -78 °C View Scheme