tetrabutyl ammonium fluoride; acetic acid in tetrahydrofuran T=0°C; 0.666667 h;

1: 85 percent / imidazole / CH2Cl2 / 20 °C 2: 100 percent / tetrabutylammonium bromide; sodium hydroxide / CH2Cl2 / 18 h / 20 °C 3: 70 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 0.67 h / 0 °C View Scheme

1) acetone, irradiation; 2) CH3OH, 10percent aq.H2SO4; Multistep reaction;

1.1: potassium carbonate / acetone / 0.25 h / 20 °C 1.2: 81 percent / acetone / 17 h / Heating 2.1: 82 percent / H2 / Pd/C / ethanol / 1 h View Scheme