sodium acetate in ethanol 3 h; Heating;

1: 90 percent / I2, aq. KI, aq. NaHCO3 / 0.5 h 2: 30 percent / NaOAc / ethanol / 3 h / Heating View Scheme

1: 1) potassium t-butoxide / 1.) t-butanol, ether, 20 min, 2.) THF, 2 h 2: 90 percent / I2, aq. KI, aq. NaHCO3 / 0.5 h 3: 30 percent / NaOAc / ethanol / 3 h / Heating View Scheme

lithium hexamethyldisilazane 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;