1: 1.) n-BuLi; 2.) Li, DTBB / 1.) THF, -78 deg C, 2 min; 2.) THF, -78 deg C, 2 h 2: H2O / 12 h / -78 - 20 °C View Scheme

1: phosphorus tribromide / CCl4 / Heating 2: ethanol / 4 h / Heating 3: aq. NaOH / ethanol / 6 h / Heating 4: H2SO4 / ethanol / 10 h / Heating 5: sodium metaperiodate / H2O; ethanol / 12 h / 0 °C 6: acetic anhydride, p-TsOH / toluene / 1 h / Heating 7: m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 8: 48 percent / pyridine / 3 h / Heating View Scheme

1: 1.) n-BuLi; 2.) Li, DTBB / 1.) THF, -78 deg C, 2 min; 2.) THF, -78 deg C, 2 h 2: H2O / 12 h / -78 - 20 °C View Scheme

phosphorus tribromide in tetrachloromethane Heating;