1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: pyridine / 15 h / -10 °C 3: Zn, sodium iodide / bis-(2-methoxy-ethyl) ether / 1.5 h / Heating 4: 10percent aq. hydrochloric acid / acetone / 6 h / Ambient temperature View Scheme

1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: pyridine / 15 h / -10 °C 3: Zn, sodium iodide / bis-(2-methoxy-ethyl) ether / 1.5 h / Heating 4: 10percent aq. hydrochloric acid / acetone / 6 h / Ambient temperature 5: diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 6: 91 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: pyridine / 15 h / -10 °C 3: Zn, sodium iodide / bis-(2-methoxy-ethyl) ether / 1.5 h / Heating 4: 10percent aq. hydrochloric acid / acetone / 6 h / Ambient temperature 5: diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 6: 87 percent / trifenylphosphine, bromine / CCl4 / 1.) 15 deg C, 1h, 2.) RT, 15 h View Scheme