in dichloromethane T=20°C; Wittig reaction; 2 h;

tributylphosphine; sodium ethanolate 1.) 95percent EtOH; 2.) -78 deg C; Yield given. Multistep reaction;

sodium hydroxide; tributylphosphine 1.) 95percent EtOH; 2.) water, r.t.; various bases and temperatures investigated; Product distribution;

1.1: boron trifluoride etherate; acetic acid / toluene / 4.5 h / 20 °C 2.1: 3.69 g / LiAlH4 / tetrahydrofuran / 1.75 h / 20 °C 3.1: 65 percent / pyridine / CH2Cl2 / 20 °C 4.1: titanocene dichloride; magnesium; triethyl phosphite / tetrahydrofuran / 0.25 h 4.2: 35 percent / tetrahydrofuran View Scheme

triphenylphosphine in methanol; water; N,N-dimethyl-formamide 1.) room temp., 30 min; 2.) ice-water bath, 30 min;

triphenylphosphine in chloroform T=20°C; 96 h;

in dichloromethane T=20°C; 1 h;