1: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 2: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 3: 30 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme

1: 91 percent 2: 1.) NaBH4; 2.) H2 / 1.) dioxane; 2.) ethanol View Scheme

1: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 2: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 3: 30 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation 4: 99 percent / pyridine / 0.17 h / 5 °C View Scheme

1: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 2: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 3: 28 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme

sodium hydroxide; potassium carbonate 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h; Yield given. Multistep reaction;

1: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 2: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 3: 30 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation 4: 96 percent / K2CO3 / dimethylformamide / 2 h / 25 °C View Scheme

1: 1) K2CO3, 2) 1 M NaOH / 1) DMSO, 25 deg C, 10 min, 2) DMSO, H2O, 25 deg C, 1 h 2: 78 percent / NaBH4 / ethanol / 3 h / 5 - 25 °C 3: 30 percent Chromat. / O2, Rose Bengal / acetonitrile / 13 °C / Irradiation 4: 96 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 5: 52 percent / CuBr2 / ethyl acetate 6: 92 percent / K2CO3 / dimethylformamide / 2 h / 25 °C 7: 90 percent / K2CO3 / dimethylsulfoxide / 0.17 h / 25 °C 8: O2, Rose Bengal / acetonitrile / 13 °C / Irradiation View Scheme