1: Nalco silica sol 1060; tris-(dibenzylideneacetone)dipalladium(0) / ethyl acetate; tetrahydrofuran; 2,4-dimethylbutane 2: magnesium sulfate; dibal / Nalco silica sol 1060 / ethyl acetate; water; tetrahydrofuran View Scheme

1: With methanol; water; sodium hydroxide 2 h; Reflux; 2: With hydrogenchloride in water pH=4 - 5;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '107195', constants.ctx, '0')">2-chloro-4-methyl-pyridine</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=-78&deg;C;&nbsp;2&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '956591', constants.ctx, '0')">ethyl carbonate</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1099903', constants.ctx, '0')">tris(dimethylamino)phosphine oxide</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=-78 - 20&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> <br /> &nbsp;