sodium hydride; triphenylphosphine in tetrahydrofuran 0.5 h; Ambient temperature;

in tetrahydrofuran 12 h; Heating; Product distribution; Further Variations:ReagentsTemperatures;

1: 1.) BF3*OEt2 / 1.) THF, 0 deg C, 5 min, 2.) THF, 0 deg C, 6 h 2: 83 percent / Ph3P, NaH / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: EtMgBr / tetrahydrofuran / 2 h / 50 °C 2: tetrahydrofuran / 1.5 h / 25 °C View Scheme

1: 48 percent / CuI / tetrahydrofuran / 0.75 h / -78 °C 2: 1.) NaBH4 / 1.) ethanol, reflux, 15 min, 2.) ethanol, RT, 30 min 3: 1.) BF3*OEt2 / 1.) THF, 0 deg C, 5 min, 2.) THF, 0 deg C, 6 h 4: 83 percent / Ph3P, NaH / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: 1.) NaBH4 / 1.) ethanol, reflux, 15 min, 2.) ethanol, RT, 30 min 2: 1.) BF3*OEt2 / 1.) THF, 0 deg C, 5 min, 2.) THF, 0 deg C, 6 h 3: 83 percent / Ph3P, NaH / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

sodium hydride; triphenylphosphine in tetrahydrofuran 0.5 h; Ambient temperature;

in tetrahydrofuran T=25°C; 1.5 h;