1: With thionyl chloride in 1,2-dichloro-ethane T=0 - 20°C; 2 h; 2: With water in 1,2-dichloro-ethane 3: With sodium hydrogencarbonate in water T=0°C; pH=8;

1.1: thionyl chloride / anhydrous dichloroethane / 2 h / 0 - 20 °C 1.2: 0 °C / pH 8 2.1: triethylamine / dichloromethane / 2 h / 0 °C View Scheme

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1918603', constants.ctx, '0')">dimethylsulfide borane complex</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '2349612', constants.ctx, '0')">boron trifluoride diethyl etherate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=80&deg;C;&nbsp;4&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098214', constants.ctx, '0')">hydrogenchloride</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;<br />Stage #3: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4153970', constants.ctx, '0')">sodium hydrogencarbonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />pH=8;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -10 &deg;C<br />1.2: 4 h / -10 - 20 &deg;C<br />2.1: dimethylsulfide borane complex; boron trifluoride diethyl etherate / tetrahydrofuran / 4 h / 80 &deg;C<br />2.2: 0 &deg;C<br />2.3: pH 8<br /> <br /> &nbsp;