sodium hydride in N,N-dimethyl-formamide T=20°C; 8 h;

sodium hydride 1.) DMF, room temp., 2 h 2.) DMF, room temp., 2 h; Yield given. Multistep reaction;

1: NaBH4 View Scheme

1: PDC 2: NaBH4 View Scheme

sodium hydride 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h; Yield given. Multistep reaction;

1: acetic acid, p-toluenesulfonic acid monohydrate / 1 h / Heating 2: 71 percent / trimethylsilyl trifluoromethanesulfonate / acetonitrile / 12 h / 55 °C 3: 86 percent / ethanolic NaOH / pyridine / 0.17 h / Ambient temperature 4: NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature 5: NaBH4 / methanol / 0.5 h / Ambient temperature 6: 68 percent / H2 / Pd black / ethanol / 9 h / 45 °C / 760 Torr View Scheme

acetic acid; periodic acid T=15°C; 0.666667 h;

1: 80percent aq. AcOH / 24 h / 25 °C 2: pyridine / CH2Cl2 / 1 h / 2 °C 3: (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 4: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C 5: p-TsOH*H2O / 3 h / 25 °C 6: NaBH4 / aq. ethanol / 2 h / 25 °C 7: 82 percent / 80percent aq. AcOH / 15 h / 80 °C 8: Pb(OAc)4 / benzene / 0.67 h / 25 °C 9: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 10: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 11: 78 percent / KF / 18-crown-6 / tetrahydrofuran / 1 h / 2 °C 12: 28percent aq. NH4OH / aq. ethanol / 0.5 h / 25 °C 13: CSA / CH2Cl2 / 1 h / 25 °C 14: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 15: 10percent aq. AcOH / acetone / 14 h / 25 °C 16: 5percent NaOMe / methanol / 2 h / 25 °C 17: Na / liquid ammonia / 0.5 h / -78 °C View Scheme

1: aq. HCl / ethanol 2: aq. NaIO4 / methanol 3: 94 percent / aq. NaOH / dioxane View Scheme