4-(N,N-dimethlyamino)pyridine; triethylamine; p-toluenesulfonyl chloride in acetonitrile T=0 - 20°C; 4 h;

1: conc. H2SO4 / 80 °C 2: 80 percent / Br2 / CCl4 / 0 - 20 °C View Scheme

1.1: conc. H2SO4 / 80 °C 2.1: 80 percent / Br2 / CCl4 / 0 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 30 h / -78 °C 3.2: triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 4.1: 70 percent / aq. Na2CO3 / Pd(PPh3)4 / ethanol / 12 h / Heating View Scheme

1.1: conc. H2SO4 / 80 °C 2.1: 80 percent / Br2 / CCl4 / 0 - 20 °C 3.1: BuLi / tetrahydrofuran; hexane / 30 h / -78 °C 3.2: triisopropyl borate / tetrahydrofuran; hexane / 2 h / -78 - 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '2805273', constants.ctx, '0')">TsNHOH</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4267587', constants.ctx, '0')">potassium carbonate</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=35&deg;C;&nbsp;24&nbsp;h;&nbsp;&nbsp;regioselective reaction;&nbsp;<br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1562059', constants.ctx, '0')">acetophenone oxime</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</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, '1730733', constants.ctx, '0')">hexane</a> <br />T=-40&deg;C;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '506104', constants.ctx, '0')">ethyl acetate</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, '1730733', constants.ctx, '0')">hexane</a> <br />T=-40 - 20&deg;C;&nbsp;&nbsp;Further stages.;&nbsp;<br /> &nbsp;