1: 80 percent / NaH / benzene / 16 h / Heating 2: 100 percent / acetic acid; water / 16 h / Heating 3: 98 percent / hexamethyldisilazane / CH2Cl2 / 17 h / 0 - 20 °C 4: 85 percent / palladium(II) acetate / acetonitrile / 16 h / 20 °C 5: Al(i-PrO)3 / 0.75 h / 130 - 140 °C 6: 550 mg / SnCl4 / CH2Cl2; nitromethane / 4 h / -78 - 20 °C 7: 81 percent / NMO; H2O / OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol / 24 h / 20 °C 8: NCS; Me2S; Et3N / CH2Cl2 / 2.5 h / -40 - 20 °C 9: 24 mg / TfOH / CH2Cl2 / 24 h / 0 °C 10: 75 percent / aluminum hydride / tetrahydrofuran / 2.5 h / 0 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587154', constants.ctx, '0')">ammonia</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3924730', constants.ctx, '0')">lithium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=-78 - 20&deg;C;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 100 percent / PTSA / toluene / Heating<br />2: 100 percent / lithium; ammonia / tetrahydrofuran / -78 - 20 &deg;C<br /> <br /> &nbsp;