in tetrahydrofuran T=0 - 20°C; 1.5 h;

cesium fluoride in acetonitrile 2 h; Ambient temperature;

cesium fluoride in acetonitrile

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 20 min 2: 1.) DIBAL, 2.) MeLi / 1.) toluene, Et2O, 0 deg C to reflux, 1 h, 2.) toluene, Et2O, 0 deg C 3: 70 percent / VO(acac)2, t-BuOOH / CH2Cl2; H2O / 2 h / Ambient temperature 4: 89 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 5: 59 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C View Scheme

1: 1.) DIBAL, 2.) MeLi / 1.) toluene, Et2O, 0 deg C to reflux, 1 h, 2.) toluene, Et2O, 0 deg C 2: 70 percent / VO(acac)2, t-BuOOH / CH2Cl2; H2O / 2 h / Ambient temperature 3: 89 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 4: 59 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C View Scheme

1: 70 percent / VO(acac)2, t-BuOOH / CH2Cl2; H2O / 2 h / Ambient temperature 2: 89 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 3: 59 percent / tetrahydrofuran / 1.5 h / 0 - 20 °C View Scheme

cesium fluoride in acetonitrile 24 h; Ambient temperatureother reagent, solvent; Product distribution;