1.1: n-BuLi / tetrahydrofuran; hexane / Heating 1.2: 45 percent / tetrahydrofuran; hexane / 20 °C 2.1: 34 percent / KOH / acetone / 20 °C View Scheme

1: ortho-N-trimethylsilyl-toluidine With n-butyllithium in tetrahydrofuran; hexane Heating; 2: methyl 2,2-dimethyl-5-hexenoate in tetrahydrofuran; hexane T=20°C;

1: isopropanol acetate With lithium diisopropyl amide in tetrahydrofuran T=-78°C; 0.5 h; 2: methyl 2,2-dimethyl-5-hexenoate in tetrahydrofuran T=25°C;

potassium hydroxide in tetrahydrofuran; methanol T=25 - 40°C; 2 h;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1740720', constants.ctx, '0')">2-methylpropanoic acid methyl ester</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '906717', constants.ctx, '0')">lithium diisopropyl amide</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 />0.333333&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '1098377', constants.ctx, '0')">4-bromo-but-1-ene</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, '1099903', constants.ctx, '0')">N,N,N',N',N'',N''-hexamethylphosphoric triamide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78&deg;C;&nbsp;12&nbsp;h;&nbsp;<br /> &nbsp;