1: (i) H2, Lindlar catalyst, PE, (ii) Ph3P, HCl, MeOH, (iii) /BRN= 2060461/, NaOMe, DMF 2: (i) H2, Lindlar catalyst, PE, (ii) (heating) View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587154', constants.ctx, '0')">ammonia</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4123684', constants.ctx, '0')">dilithium acetylide</a> <br />T=-50 - -35&deg;C;&nbsp;<br /> &nbsp;

&nbsp;(i) naphthalene/Li, THF, (ii) /BRN= 2046085/;&nbsp;&nbsp;Multistep reaction;&nbsp;<br /> &nbsp;