sodium hydride 1.) ethyl ether, reflux, 2.) ethyl ether, RT, 6 h; Multistep reaction;

1: aq. KOH / ethanol / 24 h / Heating 2: dimethylformamide / 4 h / 100 - 110 °C 3: HCl / 24 h / Ambient temperature 4: 100 percent / H2 / 5percent Pd/C / methanol / Ambient temperature 5: 0.42 g 6: 0.1 M potassium phosphate buffer (pH 7.8) / 24 h / Ambient temperature; horse liver esterase 7: iodine monochloride, 6percent aq. HCl / 1 h / 70 °C View Scheme