1.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 2.1: acetic acid / methanol / 1 h / 0 - 20 °C 2.2: 3 h / 0 - 20 °C 3.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C 4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 3 h / 20 °C / |Inert atmosphere View Scheme

1.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 2.1: acetic acid / methanol / 1 h / 0 - 20 °C 2.2: 3 h / 0 - 20 °C 3.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °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;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0 - 20&deg;C;&nbsp;1.5&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587191', constants.ctx, '0')">dihydrogen peroxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '8128150', constants.ctx, '0')">sodium hydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=0&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: zinc / tetrahydrofuran / 0.17 - 0.25 h / 20 &deg;C<br />1.2: 3 h / 0 &deg;C<br />2.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / |Reflux<br />3.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 &deg;C<br />3.2: 1 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / |Reflux<br />2.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 &deg;C<br />2.2: 1 h / 0 &deg;C<br /> <br /> &nbsp;