pyridine; trichlorophosphate in dichloromethane T=0 - 25°C;

pyridine in N-methyl-acetamide

1: 90 percent / POCl3, Py / CH2Cl2 / 0 - 25 °C 2: K3Fe(CN)6, K2CO3, OsO4, (DHQD)2-PHAL, MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 28 h / 0 °C 3: HCOONH4 / Pd-C / ethanol / 6 h / Heating 4: Jone's reagent / acetone / 8 h / 0 °C View Scheme

1: 90 percent / POCl3, Py / CH2Cl2 / 0 - 25 °C 2: K3Fe(CN)6, K2CO3, OsO4, (DHQD)2-PHAL, MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 28 h / 0 °C 3: HCOONH4 / Pd-C / ethanol / 6 h / Heating View Scheme