1: trifluoroacetic acid / dichloromethane / 20 °C 2: trifluoroacetic acid / dichloromethane / 20 °C View Scheme

trifluoroacetic acid in dichloromethane T=20°C;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11465251', constants.ctx, '0')">Jone's reagent</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635680', constants.ctx, '0')">acetone</a> <br />T=0&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 11 steps<br /> </b>1.1: n-butyllithium / tetrahydrofuran; hexanes / -75 &deg;C / Inert atmosphere<br />1.2: 1 h / -75 &deg;C<br />2.1: lithium chloride / tetrahydrofuran / 20 &deg;C<br />2.2: 1 h / -10 &deg;C / Inert atmosphere<br />3.1: hydrogen / Lindlar's catalyst / ethyl acetate<br />4.1: sodium tetrahydroborate; methanol / 0.5 h / -7 &deg;C<br />5.1: 1H-imidazole / N,N-dimethyl-formamide / Cooling with ice<br />6.1: diisobutylaluminium hydride / toluene / 1 h / -70 &deg;C / Inert atmosphere<br />7.1: n-butyllithium / tetrahydrofuran / Inert atmosphere; Cooling with ice<br />8.1: pyridinium p-toluenesulfonate / dichloromethane / 20 &deg;C<br />9.1: 9-bora-bicyclo[3.3.1]nonane; dihydrogen peroxide / tetrahydrofuran / 3 h / Inert atmosphere; Cooling with ice<br />10.1: tetrabutyl ammonium fluoride / tetrahydrofuran<br />11.1: Jone's reagent / water; acetone / 1 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 12 steps<br /> </b>1.1: 1H-imidazole / N,N-dimethyl-formamide / Cooling with ice<br />2.1: n-butyllithium / tetrahydrofuran; hexanes / -75 &deg;C / Inert atmosphere<br />2.2: 1 h / -75 &deg;C<br />3.1: lithium chloride / tetrahydrofuran / 20 &deg;C<br />3.2: 1 h / -10 &deg;C / Inert atmosphere<br />4.1: hydrogen / Lindlar's catalyst / ethyl acetate<br />5.1: sodium tetrahydroborate; methanol / 0.5 h / -7 &deg;C<br />6.1: 1H-imidazole / N,N-dimethyl-formamide / Cooling with ice<br />7.1: diisobutylaluminium hydride / toluene / 1 h / -70 &deg;C / Inert atmosphere<br />8.1: n-butyllithium / tetrahydrofuran / Inert atmosphere; Cooling with ice<br />9.1: pyridinium p-toluenesulfonate / dichloromethane / 20 &deg;C<br />10.1: 9-bora-bicyclo[3.3.1]nonane; dihydrogen peroxide / tetrahydrofuran / 3 h / Inert atmosphere; Cooling with ice<br />11.1: tetrabutyl ammonium fluoride / tetrahydrofuran<br />12.1: Jone's reagent / water; acetone / 1 h / 0 &deg;C<br /> <br /> &nbsp;