N,N,N',N'-tetramethylguanidine in acetonitrile T=20°C; 0.333333 h;

1.1: t-BuOK / dimethylformamide / 1 h / 0 °C 1.2: 54.5 percent / dimethylformamide / 8 h / 0 °C 2.1: 79 percent / (n-Bu)4NF / tetrahydrofuran / 0.75 h / 0 °C View Scheme

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1 h / -25 °C 1.2: tetrahydrofuran; hexane / -78 - 20 °C 2.1: glacial acetic acid; H2SO4 / 3 h / 95 - 100 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '110354', constants.ctx, '0')">4-(N,N-dimethlyamino)pyridine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '605283', constants.ctx, '0')">triethylamine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=20&deg;C;&nbsp;<br /> &nbsp;