Multistep reaction;

sodium hydride in ethylene glycol dimethyl ether Heating;

1: 62 percent / pyridine / Ambient temperature 2: 87 percent / 1,8-diazabicyclo<5.4.0>undecene / CH2Cl2 / Heating 3: 53 percent / iodine, silver acetate / CH2Cl2 / 0.5 h / Ambient temperature 4: 78 percent / toluene / 1.25 h / Heating 5: sodium hydride / 1,2-dimethoxy-ethane / 1.) RT, 45 min, 2.) 85 deg C, overnight View Scheme

1: 87 percent / 1,8-diazabicyclo<5.4.0>undecene / CH2Cl2 / Heating 2: 53 percent / iodine, silver acetate / CH2Cl2 / 0.5 h / Ambient temperature 3: 78 percent / toluene / 1.25 h / Heating 4: sodium hydride / 1,2-dimethoxy-ethane / 1.) RT, 45 min, 2.) 85 deg C, overnight View Scheme

1: 78 percent / toluene / 1.25 h / Heating 2: sodium hydride / 1,2-dimethoxy-ethane / 1.) RT, 45 min, 2.) 85 deg C, overnight View Scheme

1: 53 percent / iodine, silver acetate / CH2Cl2 / 0.5 h / Ambient temperature 2: 78 percent / toluene / 1.25 h / Heating 3: sodium hydride / 1,2-dimethoxy-ethane / 1.) RT, 45 min, 2.) 85 deg C, overnight View Scheme