1: 77 percent / 60percent HClO4 / diethyl ether / 1 h 2: 91 percent 3: 1.) butyllithium / 1.) -40 to -20 deg C, 2.) -70 deg C 4: 75 percent / HgO/HgCl2 / diethyl ether View Scheme

1: 77 percent / 60percent HClO4 / diethyl ether / 1 h 2: 97 percent / LiAlH4 / diethyl ether View Scheme

1: 77 percent / 60percent HClO4 / diethyl ether / 1 h 2: 97 percent / LiAlH4 / diethyl ether 3: triphenylphosphorane, bromine / 2.) pyridine, room temperature, 1 h 4: 1.) butyllithium / 1.) -65 to -30 deg C, 2.) -70 deg C 5: 57 percent / HgO/HgCl2 / diethyl ether View Scheme