thionyl chloride T=20°C; Esterification; 24 h;

nitrogen in ethanol

1: 60 percent / triphenylphosphine, DEAD / tetrahydrofuran / 0.33 h / Ambient temperature 2: 97 percent / 48 percent HBr / acetic acid / 0.75 h / Ambient temperature 3: 99 percent / hydrogen / 5 percent Pd/C / ethanol / 5 h 4: 95 percent / methanolic HCl / 18 h / Ambient temperature View Scheme

1: 76 percent / tetrakis(triphenylphosphine)-palladium(0), triphenylphosphine, pyrrolidine / CH2Cl2 / 0.17 h / Ambient temperature 2: 60 percent / triphenylphosphine, DEAD / tetrahydrofuran / 0.33 h / Ambient temperature 3: 97 percent / 48 percent HBr / acetic acid / 0.75 h / Ambient temperature 4: 99 percent / hydrogen / 5 percent Pd/C / ethanol / 5 h 5: 95 percent / methanolic HCl / 18 h / Ambient temperature View Scheme

1: 97 percent / 48 percent HBr / acetic acid / 0.75 h / Ambient temperature 2: 99 percent / hydrogen / 5 percent Pd/C / ethanol / 5 h 3: 95 percent / methanolic HCl / 18 h / Ambient temperature View Scheme

1: 99 percent / hydrogen / 5 percent Pd/C / ethanol / 5 h 2: 95 percent / methanolic HCl / 18 h / Ambient temperature View Scheme

1: 1,4-dioxane 2: triethylamine 3: lithium hydroxide hydrate; water / tetrahydrofuran View Scheme

lithium aluminium tetrahydride

triethylamine; isobutyl chloroformate in acetonitrile Ambient temperature;