1: Et3N / CH2Cl2 / 1 h / 0 °C 2: 279.8 mg / NaI / 1,2-dimethoxy-ethane / 12 h / Heating 3: 100 percent / sym-collidine / CH2Cl2 / 0.25 h / -78 °C 4: 99 percent / H2 / Rh-Al2O3 / tetrahydrofuran / 12 h / 760.05 Torr 5: 60 percent / Na(Hg) / methanol; H2O / 0.75 h 6: 75 percent / Et3N / CH2Cl2 / 0.17 h / -78 °C 7: 100 percent / H2; Et3N / Pd/C / ethyl acetate / 3 h / 760.05 Torr 8: Bu4NF / tetrahydrofuran / 12 h View Scheme

1: 64 percent / aq. NaOH / 2.5 h / 70 °C 2: 100 percent / Et3N / CH2Cl2 / 12 h / 20 °C 3: 71 percent / NaI / butan-2-one / 4 h / Heating 4: 69 percent / Bu3SnH; AIBN / toluene / 2 h / 80 °C 5: t-BuLi / hexane; tetrahydrofuran / 2 h / 20 °C 6: Na(Hg) / methanol; H2O / 12 h View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4267587', constants.ctx, '0')">potassium carbonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />2.5&nbsp;h;&nbsp;<br /> &nbsp;