1.1: sodium hydride / toluene / 1 h / 20 °C / Inert atmosphere 1.2: 4 h / 45 - 50 °C 1.3: 0 - 5 °C / pH 1 2.1: lithium chloride / dimethyl sulfoxide / 15 h / 150 - 160 °C 3.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 3.2: pH 1 4.1: di-isopropyl ether / 6 h / 20 - 75 °C 5.1: hydrogenchloride / water; tert-butyl methyl ether / 0.5 h / 20 - 25 °C 6.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 7.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 8.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 8.2: 0.5 h / 0 - 5 °C View Scheme

1.1: sodium hydride / toluene / 1 h / 20 °C / Inert atmosphere 1.2: 4 h / 45 - 50 °C 1.3: 0 - 5 °C / pH 1 2.1: lithium chloride / dimethyl sulfoxide / 15 h / 150 - 160 °C 3.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 3.2: pH 1 4.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 5.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 6.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 6.2: 0.5 h / 0 - 5 °C 7.1: hydrogen bromide / water / 3 h / 90 - 100 °C 8.1: (2S,3S)-(+)-di-O-benzoyl tartaric acid / isobutyl methylketone; methanol / 25 °C 8.2: pH 8 View Scheme

Stage #1: &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=-15 - 25&deg;C;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4371014', constants.ctx, '0')">ammonium chloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=0 - 5&deg;C;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 6 h / 50 - 60 &deg;C<br />2.1: tetrahydrofuran / -15 - 25 &deg;C / Inert atmosphere<br />2.2: 0 - 5 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 6 h / 50 - 60 &deg;C<br />2.1: tetrahydrofuran / -15 - 25 &deg;C / Inert atmosphere<br />2.2: 0 - 5 &deg;C<br /> <br /> &nbsp;