1: 91 percent / pyridine, 4-dimethylaminopyridine / 12 h / Ambient temperature 2: 82 percent / hydrogen / 10percent Pd/C / ethyl acetate / 5 h / Ambient temperature 3: 99 percent / dimethyl sulfoxide, oxalyl chloride / CH2Cl2 / 0.25 h / -78 °C 4: zinc powder, acetic acid / tetrahydrofuran; H2O / 30 h / Ambient temperature 5: zinc chloride / CH2Cl2 / 0.17 h / Ambient temperature 6: 81 percent / trifluoroacetic acid / CH2Cl2 / 5 h / Ambient temperature 7: 68 percent / N,N-diisopropylethylamine / acetonitrile / 3 h / 60 °C 8: 79 percent / 2.6 M Jones reagent, celite / acetone / 0.5 h / Ambient temperature 9: 88 percent / sodium hydroxide / methanol / 2 h / Ambient temperature 10: 81 percent / silver nitrate / methanol / 1 h / Ambient temperature View Scheme