1: 88 percent / Et3N / CH2Cl2 2: 82 percent / Li; NH3 / tetrahydrofuran / 1 h / -40 °C 3: 84 percent / Et3N / CH2Cl2 / 2 h / 20 °C 4: 87 percent / NaH / tetrahydrofuran / 24 h / 40 °C 5: 68 percent / aq. NaN3; NH4Cl / ethanol / 48 h / Heating 6: 99 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C 7: NMO monohydrate; OsO4; H2O / 2-methyl-propan-2-ol; acetone / 14 h / 20 °C 8: KBr; TBAB; aq. NaHCO3 / Ca(ClO)2; TEMPO / 16 - 20 °C 9: 120 mg / K2CO3 / dimethylformamide / 4 h / 20 °C 10: Dess-Martin periodinane / CH2Cl2 / 0 - 20 °C 11: 118 mg / aq. HF / acetonitrile / 4 h / 30 °C 12: 65 percent / pyridine / 12 h / 20 °C 13: 74 percent / HCl / CH2Cl2 / 14 h / -40 - 20 °C 14: 98 percent / DBU / CH2Cl2 / 1 h / 10 °C View Scheme