sodium hydroxide in water T=20°C; Wittig reaction; 18 h;

1.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 1.2: 51 percent / tetrahydrofuran / 18 h / 20 °C 2.1: 93 percent / NaBH4 / ethanol / 6 h / 20 °C 3.1: 85 percent / SOCl2 / benzene / 4 h / 50 °C 4.1: 90 percent / dimethylformamide / 5 h / 100 °C 5.1: 86 percent / NaOH / H2O / 18 h / 20 °C View Scheme

1: 93 percent / NaBH4 / ethanol / 6 h / 20 °C 2: 85 percent / SOCl2 / benzene / 4 h / 50 °C 3: 90 percent / dimethylformamide / 5 h / 100 °C 4: 86 percent / NaOH / H2O / 18 h / 20 °C View Scheme

1: 90 percent / dimethylformamide / 5 h / 100 °C 2: 86 percent / NaOH / H2O / 18 h / 20 °C View Scheme

1: 85 percent / SOCl2 / benzene / 4 h / 50 °C 2: 90 percent / dimethylformamide / 5 h / 100 °C 3: 86 percent / NaOH / H2O / 18 h / 20 °C View Scheme

bis-triphenylphosphine-palladium(II) chloride; 2,6-di-tert-butyl-phenol in toluene Stille coupling;