1: 80 percent / HClO4 / Ambient temperature 2: N-bromosuccinimide (NBS) / CCl4 / Irradiation 3: 18-crown-6 / acetonitrile 4: 1.)NaH / 1.) THF, -15 deg C to -10 deg C, 1h; 2.) THF, -30 deg C to -20 deg C, 10h 5: Al(Hg) / tetrahydrofuran; H2O / Ambient temperature View Scheme

1: N-bromosuccinimide (NBS) / CCl4 / Irradiation 2: 18-crown-6 / acetonitrile 3: 1.)NaH / 1.) THF, -15 deg C to -10 deg C, 1h; 2.) THF, -30 deg C to -20 deg C, 10h 4: Al(Hg) / tetrahydrofuran; H2O / Ambient temperature View Scheme

1: 18-crown-6 / acetonitrile 2: 1.)NaH / 1.) THF, -15 deg C to -10 deg C, 1h; 2.) THF, -30 deg C to -20 deg C, 10h 3: Al(Hg) / tetrahydrofuran; H2O / Ambient temperature View Scheme

aluminum amalgam in tetrahydrofuran; water Ambient temperature; Yield given;

1: 1.)NaH / 1.) THF, -15 deg C to -10 deg C, 1h; 2.) THF, -30 deg C to -20 deg C, 10h 2: Al(Hg) / tetrahydrofuran; H2O / Ambient temperature View Scheme