1: 77 percent / pyridine; CH2Cl2 / 2 h / -15 °C 2: 76 percent / Tetra-n-butylammonium fluoride (TBAF) / tetrahydrofuran / 1.) -10 deg C, 2.) ice bath-cooling, 5 h; other salts of var. nucleophiles as reagents View Scheme

1: sodium hypochlorite; TEMPO / 0 °C 2: 78.3 percent / diethyl ether / -78 °C 3: 19.3 percent / (diethylamino)sulfur trifluoride / CH2Cl2 / 20 °C 4: cyclohexene / palladium on carbon / ethanol; ethyl acetate / Heating 5: 0.350 g / pyridine / 20 °C 6: 52.1 percent / formic acid / H2O / 48 h / 60 - 70 °C 7: 88.7 percent / triethylamine / CH2Cl2 / 20 °C 8: 37 percent / tin(IV) chloride / acetonitrile / 4 h / 50 - 55 °C View Scheme

1: trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et3SiH / CH2Cl2 / Ambient temperature 2: 97 percent / DMAP, Et3N / CH2Cl2 / 2 h / Ambient temperature 3: 49.5 percent / K2CO3, 18-crown-6 / dimethylformamide / 20 h / 120 °C 4: 78 percent / BCl3 / hexane; CH2Cl2 / 1.) -78 deg C, 2.5 h; 2.) -18 deg C, 4 h View Scheme