1: oxalyl chloride / CH2Cl2; dimethylformamide / 0.75 h / 0 °C 2: 22 percent / 1M sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C 3: 99 percent / H2 / Lindlar's catalyst / benzene / 0.33 h / 760 Torr 4: 53 percent / lithium diisopropylaminde / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -108 °C 5: 70 percent Turnov. / 1M triethylaluminum, tetrakis(triphenylphosphine)palladium(0) / hexane; 1,2-dichloro-ethane / 10.5 h / 20 °C 6: 96 percent / KOH / H2O; methanol / 4 h / Heating 7: triethylamine / CH2Cl2 / 0.5 h / -23 °C 8: 100 percent / NaCN / dimethylsulfoxide / 5 h / 20 °C 9: KOH / ethanol / 5 h / Heating View Scheme

<b>Multi-step reaction with 2 steps<br /> </b>1: 88 percent / CHCl₃; pyridine / 1.)0 deg C, 1 h, 2.)22 deg C, 14 h<br />2: 96 percent / K₂CO₃, H₂O / methanol / 1 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 88 percent / CHCl₃; pyridine / 1.)0 deg C, 1 h, 2.)22 deg C, 14 h<br />2: 96 percent / K₂CO₃, H₂O / methanol / 1 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 98 percent / NaBH₄ / ethanol / 0.33 h / 0 &deg;C<br />2: 88 percent / CHCl₃; pyridine / 1.)0 deg C, 1 h, 2.)22 deg C, 14 h<br />3: 96 percent / K₂CO₃, H₂O / methanol / 1 h / Heating<br /> <br /> &nbsp;