1: 1.) BuLi / 1.) THF, hexane, from -80 deg C to RT, 2.) THF, hexane, RT, 4 h 2: 100 percent / 0.1N HCl / methanol / 6 h 3: 67 percent / CBr4, PPh3 / CH2Cl2 / 2 h / 0 °C View Scheme

1: 1.) BuLi / 1.) THF, hexane, from -80 deg C to RT, 2.) THF, hexane, RT, 4 h 2: 100 percent / 0.1N HCl / methanol / 6 h 3: 67 percent / CBr4, PPh3 / CH2Cl2 / 2 h / 0 °C 4: 100 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

1: 1.) BuLi / 1.) THF, hexane, from -80 deg C to RT, 2.) THF, hexane, RT, 4 h 2: 100 percent / 0.1N HCl / methanol / 6 h View Scheme

1: tetrahydrofuran / 3 h / 0 °C 2: 48percent HBr / acetic acid / Heating 3: 100 percent / NaBH4 / methanol / 1 h / Ambient temperature 4: 89 percent / acetonitrile / 5 h / 60 °C View Scheme