1: 12 percent / pyridinium chlorochromate / CH2Cl2 / 55 h / Ambient temperature 2: 69 percent / pyridinium chlorochromate / CH2Cl2 / 60 h / Heating 3: 59 percent / hydrogen / 10 percent Pd/C / acetic acid / 24 h / Ambient temperature View Scheme

triethylamine in dichloromethane 192 h; Ambient temperature;

pyridinium chlorochromate in dichloromethane 55 h; Ambient temperature;

n-butyllithium; N,N,N',N,-tetramethylethylenediamine 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, up to r. t., 15 h; Yield given. Multistep reaction. Yields of byproduct given;