2: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating 3: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1 h 2.) THF, -100 deg C to 0 deg C 4: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating 5: 1.) LiAlH4 2.) 2N HCl, H2O / 1.) THF, -70 deg C 2.) -20 deg C 6: 95 percent / CBr4, triphenylphosphine / CH2Cl2 / -5 °C 7: 74 percent / acetonitrile / 36 h / Heating 8: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1.5 h 2.) THF, -100 deg C View Scheme

1: 1.) LiAlH4 2.) 2N HCl, H2O / 1.) THF, -70 deg C 2.) -20 deg C 2: 95 percent / CBr4, triphenylphosphine / CH2Cl2 / -5 °C 3: 74 percent / acetonitrile / 36 h / Heating 4: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1.5 h 2.) THF, -100 deg C View Scheme

1: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1 h 2.) THF, -100 deg C to 0 deg C 2: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating 3: 1.) LiAlH4 2.) 2N HCl, H2O / 1.) THF, -70 deg C 2.) -20 deg C 4: 95 percent / CBr4, triphenylphosphine / CH2Cl2 / -5 °C 5: 74 percent / acetonitrile / 36 h / Heating 6: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1.5 h 2.) THF, -100 deg C View Scheme

1: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating 2: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1 h 2.) THF, -100 deg C to 0 deg C 3: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating 4: 1.) LiAlH4 2.) 2N HCl, H2O / 1.) THF, -70 deg C 2.) -20 deg C 5: 95 percent / CBr4, triphenylphosphine / CH2Cl2 / -5 °C 6: 74 percent / acetonitrile / 36 h / Heating 7: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1.5 h 2.) THF, -100 deg C View Scheme

1: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating 2: 1.) LiAlH4 2.) 2N HCl, H2O / 1.) THF, -70 deg C 2.) -20 deg C 3: 95 percent / CBr4, triphenylphosphine / CH2Cl2 / -5 °C 4: 74 percent / acetonitrile / 36 h / Heating 5: 1.) NaN(SiMe3)2 / 1.) THF, toluene, r.t., 1.5 h 2.) THF, -100 deg C View Scheme

1: MnO2 / CH2Cl2 / 24 h / 20 °C 2: 1.) BuLi / 1.) THF, hexane, 2.) THF, hexane, 20 deg C, 4 h View Scheme

Na-Silazid Yield given. Multistep reaction;

1: 68 percent 2: 1.) EtMgBr 3: 1.) EtMgBr 4: 1.)CBr4/TPP; 2.)NaI 5: 52 percent 6: 1.) Na-Silazid View Scheme

n-butyllithium 1.) THF, hexane, 2.) THF, hexane, 20 deg C, 4 h; Yield given. Multistep reaction;