chloro-trimethyl-silane 2 h; Heating;

1: 75 percent / tributyltin hydride; NaI; AIBN / 1,2-dimethoxy-ethane / 12 h / Heating 2: 61 percent / TMSCl / 2 h / 50 °C View Scheme

1: 12 g / potassium hydroxide; tetra-n-butylammonium hydrogen sulfate / CHCl3 / 18 h 2: 75 percent / tributyltin hydride; NaI; AIBN / 1,2-dimethoxy-ethane / 12 h / Heating 3: 61 percent / TMSCl / 2 h / 50 °C View Scheme

1: 82 percent / SOCl2 / 1.) room temp., 30 min, 2.) reflux, 90 min; 130 deg C 2: NaBH4 / H2O / 1.5 h / Ambient temperature 3: KOH, Bu4NHSO4 / CHCl3 / 48 h / Irradiation 4: 53 percent / NaI, Bu3SnH, AIBN / 1,2-dimethoxy-ethane / 12 h / Heating 5: 82 percent / Me3SiCl / 2 h / Heating View Scheme

1: NaBH4 / H2O / 1.5 h / Ambient temperature 2: KOH, Bu4NHSO4 / CHCl3 / 48 h / Irradiation 3: 53 percent / NaI, Bu3SnH, AIBN / 1,2-dimethoxy-ethane / 12 h / Heating 4: 82 percent / Me3SiCl / 2 h / Heating View Scheme

1.1: 82 percent / thionyl chloride / 1 h 2.1: sodium borohydride / H2O / 20 °C 2.2: H2O; acetone / 0 °C 3.1: 12 g / potassium hydroxide; tetra-n-butylammonium hydrogen sulfate / CHCl3 / 18 h 4.1: 75 percent / tributyltin hydride; NaI; AIBN / 1,2-dimethoxy-ethane / 12 h / Heating 5.1: 61 percent / TMSCl / 2 h / 50 °C View Scheme