n-butyllithium in tetrahydrofuran; hexane 1) -78 deg C, 10 min 2) r.t., 90 min;

sulfuric acid 18 h; Heating;

1: 47.5 percent / H2SO4 conc. / 18 h / Heating 2: 96 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 3: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature 4: 79.6 percent / H2 / Pd/C / ethyl acetate / 4 h / 760 Torr / Ambient temperature View Scheme

1: 47.5 percent / H2SO4 conc. / 18 h / Heating 2: 96 percent / CrO3, pyridine / CH2Cl2 / 0.33 h 3: 89.7 percent / NaH, Me2SO / 24 h / Ambient temperature View Scheme