in ethylene glycol dimethyl ether

sodium hydride 1) DME, r.t. 2) DME, 65 deg C, 48 h; Yield given. Multistep reaction;

water; oxalic acid; silica gel in dichloromethane 0.25 h; Ambient temperature;

1: 100 percent / SiO2, H2O, oxalic acid / CH2Cl2 / 0.25 h / Ambient temperature 2: 1) Mg / 1) ether 2) ether, 0 deg C, 15 min then 0 deg C to room temp., 30 min 3: 81 percent / MnO2 active / CH2Cl2 / 16 h / Ambient temperature View Scheme

sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid in dichloromethane 1.5 h; Ambient temperature;

1: 100 percent / SiO2, H2O, oxalic acid / CH2Cl2 / 0.25 h / Ambient temperature 2: 1) Mg / 1) ether 2) ether, 0 deg C, 15 min then 0 deg C to room temp., 30 min 3: 50 percent / MnO2 active / CH2Cl2 / 120 h / Ambient temperature View Scheme