1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 60 °C / Inert atmosphere 2.1: sodium tetrahydroborate / ethanol / 20 °C / Inert atmosphere; Cooling with acetone-dry ice 2.2: Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / -78 °C / Inert atmosphere; Reflux 4.1: potassium carbonate / acetone / 6 h / Inert atmosphere; Reflux View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3903207', constants.ctx, '0')">titanium tetrachloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-20 - 0&deg;C;&nbsp;Friedel Crafts acylation;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;