1: 95 percent / ammonium acetate / acetic acid / 3 h / Heating 2: 80 percent / LiAlH4, AlCl3 / tetrahydrofuran / 16 h / Ambient temperature 3: Me3SiI / CHCl3; tetrahydrothiophene 1,1-dioxide / 72 h / 50 °C View Scheme

1: 1.) N,N,N'-trimethylethylenediamine, n-BuLi, 2.) hexachloroethane / 1.) THF, from -70 deg C to -30 deg C, 8 h, 2.) THF, RT, 3 h 2: 95 percent / ammonium acetate / acetic acid / 3 h / Heating 3: 80 percent / LiAlH4, AlCl3 / tetrahydrofuran / 16 h / Ambient temperature 4: Me3SiI / CHCl3; tetrahydrothiophene 1,1-dioxide / 72 h / 50 °C View Scheme

1: 67 percent / 18-crown-6 / acetonitrile / 168 h / Heating 2: 51 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 3: Me3SiI / CHCl3; tetrahydrothiophene 1,1-dioxide / 72 h / 50 °C View Scheme

1: 51 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 2: Me3SiI / CHCl3; tetrahydrothiophene 1,1-dioxide / 72 h / 50 °C View Scheme

1: 80 percent / LiAlH4, AlCl3 / tetrahydrofuran / 16 h / Ambient temperature 2: Me3SiI / CHCl3; tetrahydrothiophene 1,1-dioxide / 72 h / 50 °C View Scheme

1: 84 percent / SOCl2 / 24 h / Heating 2: 67 percent / 18-crown-6 / acetonitrile / 168 h / Heating 3: 51 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 4: Me3SiI / CHCl3; tetrahydrothiophene 1,1-dioxide / 72 h / 50 °C View Scheme