acetic acid in methanol; water 3 h; Heating;

1: 82 percent / H2 / 10percent Pd/C / ethanol / 2 h / 50 °C / 1034.3 Torr 2: 1.) NaH / 1.) pentane, THF, RT, a) 1 h, reflux, b) 1 h, 2.) RT, 3 h 3: 1.) t-BuLi / 1.) THF, -78 deg C, 1 h, 2.) a.) -78 deg C, 10 min, b) RT, 1 h 4: 0.08 g / TFA / CH2Cl2 / 4 h / Ambient temperature View Scheme