pyridine; trichlorophosphate 1.) room temperature, 3 h, 2.) reflux, 10 min;

1: 1.) Na, 2.) H3O(1+), 3.) H(1+) / 1.) toluene, 3.) C6H6 2: 1.) H(1+), 2.) LiAlH4 / 1.) C6H6, 2.) THF, 3.) Collins, CH2Cl2 3: 94 percent 4: 92 percent / Al2O3 / tetrahydrofuran / 10 h / 40 °C 5: 91 percent / diethyl ether / 0 °C 6: 97 percent / aq. H2SO4 / tetrahydrofuran / Heating 7: aq. AcOH, EtOH / 0 °C 8: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme

1: 1.) H(1+), 2.) LiAlH4 / 1.) C6H6, 2.) THF, 3.) Collins, CH2Cl2 2: 94 percent 3: 92 percent / Al2O3 / tetrahydrofuran / 10 h / 40 °C 4: 91 percent / diethyl ether / 0 °C 5: 97 percent / aq. H2SO4 / tetrahydrofuran / Heating 6: aq. AcOH, EtOH / 0 °C 7: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme

1: 94 percent 2: 92 percent / Al2O3 / tetrahydrofuran / 10 h / 40 °C 3: 91 percent / diethyl ether / 0 °C 4: 97 percent / aq. H2SO4 / tetrahydrofuran / Heating 5: aq. AcOH, EtOH / 0 °C 6: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme

1: 91 percent / diethyl ether / 0 °C 2: 97 percent / aq. H2SO4 / tetrahydrofuran / Heating 3: aq. AcOH, EtOH / 0 °C 4: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme

1: 97 percent / aq. H2SO4 / tetrahydrofuran / Heating 2: aq. AcOH, EtOH / 0 °C 3: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme

1: 92 percent / Al2O3 / tetrahydrofuran / 10 h / 40 °C 2: 91 percent / diethyl ether / 0 °C 3: 97 percent / aq. H2SO4 / tetrahydrofuran / Heating 4: aq. AcOH, EtOH / 0 °C 5: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme

1: aq. AcOH, EtOH / 0 °C 2: 92 percent / POCl3, py / 1.) room temperature, 3 h, 2.) reflux, 10 min View Scheme