1: 80 percent / tetrahydrofuran / -78 deg C, 2 h. then 22 deg C, 14 h. 2: 94 percent / 2N sulfuric acid / acetic acid; H2O; tetrahydrofuran / 24 h / Ambient temperature 3: 87 percent / diethyl ether; pyridine / 0 deg C, 2 h. then 22 deg C, 24 h. 4: 77 percent / triphenylphosphine, diethylazodicarboxylate / tetrahydrofuran / 22 °C 5: N-methylmorpholine N-oxide hydrate, osmium tetroxide / H2O; 2-methyl-propan-2-ol; acetone / 24 h / 22 °C 6: 79 percent / hydrazine hydrate / ethanol / 2 h / 60 °C 7: 85 percent / aq. KOH / methanol / 22 deg C, 12 h. then 60 deg C, 3 h. View Scheme

sodium hexamethyldisilazane in tetrahydrofuran T=-75°C;