ammonium cerium(IV) nitrate in water; acetonitrile T=0°C; Oxidation; 2.16667 h;

1: 92 percent / BF3*OEt2 / toluene 2: 100 percent / triethylamine / methanol / 7 h / 70 °C 3: 99 percent / Pseudomonas lipase PS / 48 h / 20 °C 4: 100 percent / 1,8-diazabicyclo[5.4.0]-7-undecene / CH2Cl2 / 0.25 h / -17 °C 5: 54 percent / molecular sieves 4A / diphenyl ether / 0.58 h / 210 °C 6: 77 percent / ruthenium(III) chloride trihydrate; sodium metaperiodate / acetonitrile; ethyl acetate; H2O / 0.07 h / -11 °C 7: aq. sodium hydroxide / ethanol / 2 h / 30 - 40 °C 8: 42.8 mg / pyridine; DMAP / 20 °C 9: 87 percent / triethylamine / methanol / 7 h / 20 °C 10: 29.5 percent / diammonium cerium(IV) nitrate / acetonitrile; H2O / 2.17 h / 0 °C View Scheme

1: aq. sodium hydroxide / ethanol / 2 h / 30 - 40 °C 2: 42.8 mg / pyridine; DMAP / 20 °C 3: 87 percent / triethylamine / methanol / 7 h / 20 °C 4: 29.5 percent / diammonium cerium(IV) nitrate / acetonitrile; H2O / 2.17 h / 0 °C View Scheme