sodium hydride 1.) DMF, 30 min, 2.) DMF, RT, 2 h; Yield given. Multistep reaction;

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 3: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 4: 71.3 percent / acetonitrile / 14 h / Heating 5: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 6: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 3: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 4: 71.3 percent / acetonitrile / 14 h / Heating 5: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 3: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 3: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 4: 71.3 percent / acetonitrile / 14 h / Heating View Scheme