lithium hydroxide in 1,4-dioxane; water T=40°C; 1 h;

in 1,4-dioxane; water

1: 32 percent / pyridine / CH2Cl2 / Ambient temperature 2: 1.) 9-BBN, 2.) 1M aq. NaOH, 27percent aq. H2O2 / 1.) THF, RT, 3 h, 2.) THF, 40 deg C, 1 h 3: CBr4, PPh3 / CH2Cl2 / 2 h / Ambient temperature 4: 1.) NaH, 2.) KI / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 4 h 5: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 6: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme

1: SOCl2 / 1 h / Ambient temperature 2: 32 percent / pyridine / CH2Cl2 / Ambient temperature 3: 1.) 9-BBN, 2.) 1M aq. NaOH, 27percent aq. H2O2 / 1.) THF, RT, 3 h, 2.) THF, 40 deg C, 1 h 4: CBr4, PPh3 / CH2Cl2 / 2 h / Ambient temperature 5: 1.) NaH, 2.) KI / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 4 h 6: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 7: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme

1: 32 percent / pyridine / CH2Cl2 / Ambient temperature 2: 1.) 9-BBN, 2.) 1M aq. NaOH, 27percent aq. H2O2 / 1.) THF, RT, 3 h, 2.) THF, 40 deg C, 1 h 3: CBr4, PPh3 / CH2Cl2 / 2 h / Ambient temperature 4: 1.) NaH, 2.) KI / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 4 h 5: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 6: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme

1: 88 percent / acetyl chloride / 1 h / Heating 2: 32 percent / pyridine / CH2Cl2 / Ambient temperature 3: 1.) 9-BBN, 2.) 1M aq. NaOH, 27percent aq. H2O2 / 1.) THF, RT, 3 h, 2.) THF, 40 deg C, 1 h 4: CBr4, PPh3 / CH2Cl2 / 2 h / Ambient temperature 5: 1.) NaH, 2.) KI / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 4 h 6: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 7: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme

1: 1.) 9-BBN, 2.) 1M aq. NaOH, 27percent aq. H2O2 / 1.) THF, RT, 3 h, 2.) THF, 40 deg C, 1 h 2: CBr4, PPh3 / CH2Cl2 / 2 h / Ambient temperature 3: 1.) NaH, 2.) KI / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 4 h 4: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 5: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme

1: CBr4, PPh3 / CH2Cl2 / 2 h / Ambient temperature 2: 1.) NaH, 2.) KI / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 4 h 3: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 4: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme

1: 1.) NaH, 2.) KI / 1.) DMF, RT, 10 min, 2.) DMF, 70 deg C, 4 h 2: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 3: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme

1: 90 percent / borane-THF complex / tetrahydrofuran / 1 h / Heating 2: 90 percent / LiOH*H2O / dioxane; H2O / 1 h / 40 °C View Scheme