1: 67 percent / LiAlH4 / tetrahydrofuran / 10 h / Heating 2: 87 percent / Zn / acetic acid / 4 h / 50 - 60 °C 3: 90 percent / H2 / 5percent Pd on charcoal / methanol / 16 h 4: 1.) SOCl2, 2.) TABD / 1.) CDCl3, 0 deg C to room temperature, 19.5 h, 2.) 12 h View Scheme

1: 90 percent / 45percent HBr(AcOH) / 2 h / Ambient temperature 2: 64 percent / Zn, AcOH / 4 h / 50 - 60 °C 3: 1.) NaH / 1.) Et2O, r. t., 2 h, 2.) r. t., 2 h 4: 93 percent / pyridine / CH2Cl2 / 2 h / 0 °C 5: 64 percent / NEt3, Ph3P, Pd2(dba)3*CHCl3 / tetrahydrofuran / 14 h / Heating View Scheme

hydrogen bromide 2 h; Ambient temperature;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '16308551', constants.ctx, '0')">tetramethylammonium metaperiodate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br /> <br /> &nbsp;