1: 98 percent / quinoline, H2 / Lindlar catalyst / hexane / 1 h / Ambient temperature 2: 96 percent / Ph3P, imidazole, I2 / tetrahydrofuran / -30 - 20 °C 3: 100 percent / calcium carbonate / acetonitrile / 72 h / 40 °C 4: 1.) n-BuLi / 1) THF, hexane, -45 deg C, 30 min; 2) THF, hexane, HMPA, -78 deg C, 30 min; 3) THF, hexane, HMPA, -78 deg C --> rt 5: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature 6: 95 percent / Ph3P, imidazole iodine / tetrahydrofuran / 1 h / Ambient temperature 7: 100 percent / calcium carbonate / acetonitrile / 72 h / 50 °C 8: 1.) n-BuLi / 1) THF, hexane, -78 --> -40 deg C, 45 min; 2) THF, HMPA, hexane, -78 deg C --> rt, 90 min 9: 100 percent / aq. CF3CO2H / CH2Cl2 / 0.5 h / 0 °C 10: 1.) n-BuLi / 1) THF, hexane, -78 deg C --> rt; 2) THF, hexane, HMPA, -78 deg C --> rt, 60 min View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '2349612', constants.ctx, '0')">boron trifluoride diethyl etherate</a> <br />&nbsp;1) THF, hexane, -78 deg C, 10 min; 2) THF, hexane, -78 deg C, 10 min; 3) THF, hexane, -78 deg C, 1 h;&nbsp;&nbsp;Yield given. Multistep reaction;&nbsp;<br /> &nbsp;