sulfuric acid in methanol T=23°C; 2 h;

1: 97 percent / H2SO4 / methanol / 2 h / 23 °C 2: benzophenone / 4 h / 0 °C / UV-irradiation 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C 7: 66 percent / Et3N / acetonitrile / 7 h / 23 °C View Scheme

1: 97 percent / H2SO4 / methanol / 2 h / 23 °C 2: benzophenone / 4 h / 0 °C / UV-irradiation 3: LiAlH4 / tetrahydrofuran / 4 h / 0 °C 4: 145 mg / HCl / tetrahydrofuran; H2O / 40 h / 23 °C / pH 2 - 3 5: triphenylphosphine; diisopropyl azodicarboxylate / benzene / 1.5 h / 23 °C 6: 326 mg / LiOH; Et3N / methanol; H2O / 2 h / 23 °C View Scheme

in methanol T=0°C; Condensation; Wittig reaction; 1 h;

triethylamine in dichloromethane T=20°C; 1 h;

1: 98 percent / NaIO4; NaHCO3 / CH2Cl2 / 1.5 h / 20 °C 2: methanol / 20 h / -10 °C View Scheme

potassium carbonate in water; ethyl acetate T=20°C; Wittig Reaction; 12 h; Product distribution / selectivity;

in methanol Ambient temperature;

sodium hydroxide in ethylene glycol dimethyl ether; pentane 2 h; Ambient temperature;

1: 80 percent / DIBAL-H / CH2Cl2 / 4 h / 0 °C 2: 99 percent / Et3N / CH2Cl2 / 1 h / 20 °C View Scheme