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: 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 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 View Scheme

Multi-step reaction with 2 steps 2: 0.1 M aq. p-toluenesulfonic acid / tetrahydrofuran / 0.3 h / Heating