1: 53 percent / I2, AgOAc 2: 78 percent 3: 59 percent Chromat. / NaH / 1,2-dimethoxy-ethane / Heating 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