1: 81 percent / HCl / Ambient temperature 2: 91 percent / conc aq. NH4OH / Ambient temperature 3: 75 percent / 5percent Pd/C / xylene / 4 h / Heating 4: 77 percent / POCl3 / toluene / Heating 5: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h 6: 74 percent / 17.5percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature 7: 75 percent / borane-trimethylamine / tetrahydrofuran; acetic acid / 1 h / 0 °C 8: 1.) aq. NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

hydrazine in ethanol; benzene

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene Ambient temperature;

1: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h 2: 74 percent / 17.5percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature 3: 75 percent / borane-trimethylamine / tetrahydrofuran; acetic acid / 1 h / 0 °C 4: 1.) aq. NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

1: 75 percent / borane-trimethylamine / tetrahydrofuran; acetic acid / 1 h / 0 °C 2: 1.) aq. NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

1: 74 percent / 17.5percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature 2: 75 percent / borane-trimethylamine / tetrahydrofuran; acetic acid / 1 h / 0 °C 3: 1.) aq. NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

1: 77 percent / POCl3 / toluene / Heating 2: 2.) NaBH4 / 1.) THF, r.t., 1 h, 2.) THF, MeOH, 0 deg C, 0.5 h 3: 74 percent / 17.5percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature 4: 75 percent / borane-trimethylamine / tetrahydrofuran; acetic acid / 1 h / 0 °C 5: 1.) aq. NaOCl, 2.) Na2CO3 / 1.) MeOH, 10 min, 2.) MeOH, 1 h View Scheme

sodium hypochlorite; sodium carbonate 1.) MeOH, 10 min, 2.) MeOH, 1 h; Yield given. Multistep reaction;

1: 74 percent / NaOH / H2O; CH2Cl2 / 1 h 2: 74 percent / PPE / CH2Cl2 / 0.83 h / Heating 3: 90 percent / DDQ / benzene / Ambient temperature View Scheme

1: 74 percent / PPE / CH2Cl2 / 0.83 h / Heating 2: 90 percent / DDQ / benzene / Ambient temperature View Scheme