1: TsOH / tetrahydrofuran; H2O / 0.17 h 2: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 3: 92 percent / LiOH / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: TsOH / tetrahydrofuran; H2O / 0.17 h 2: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT View Scheme

1.1: p-toluenesulfonic acid / tetrahydrofuran; H2O / 0.33 h / Heating 2.1: sodium bis(trimetylsilyl)amide / tetrahydrofuran / 1 h / 0 °C 2.2: 53 percent / tetrahydrofuran / -100 - 20 °C 3.1: p-toluenesulfonic acid / tetrahydrofuran; H2O / 0.25 h / Heating View Scheme

1: p-toluenesulfonic acid / tetrahydrofuran; H2O / 0.33 h / Heating 2: 91 percent / sodium borohydride / methanol / 0.17 h / 0 °C 3: 86 percent / triphenylphosphine; carbon tetrabromide / CH2Cl2 / 2 h / 20 °C View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: 73 percent / LiAlH₄ / tetrahydrofuran / -70 to -30 deg C<br />2: 91 percent / Ph₃PBr₂, pyridine / acetonitrile / 1 h / 0 deg C to RT<br />3: 60 percent / NEt₃, NaI / acetonitrile / 15 h / 85 &deg;C<br />4: 80 percent / NaN(SiMe₃)2 / tetrahydrofuran / -100 deg C to RT<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 60 percent / NEt₃, NaI / acetonitrile / 15 h / 85 &deg;C<br />2: 80 percent / NaN(SiMe₃)2 / tetrahydrofuran / -100 deg C to RT<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3629917', constants.ctx, '0')">sodium hexamethyldisilazane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />&nbsp;-100 deg C to RT;&nbsp;<br /> &nbsp;