1: 70 percent / LiAlH4, AlCl3 / diethyl ether / 1 h / Ambient temperature 2: 55 percent / isoamyl nitrite / CH2Cl2; tetrahydrofuran / 1.5 h / Heating 3: conc. HCl / methanol / 16 h / Heating View Scheme

lithium aluminium tetrahydride; aluminium trichloride in diethyl ether 1 h; Ambient temperature;

chloro-trimethyl-silane; sodium iodide in acetonitrile 0 deg C to 10 deg C, 30 min then r.t.;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '105337', constants.ctx, '0')">3-bromo-furan</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;0.25&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '471223', constants.ctx, '0')">benzaldehyde</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;&nbsp;Further stages.;&nbsp;<br /> &nbsp;

&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;3&nbsp;h;&nbsp;<br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587194', constants.ctx, '0')">iodine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4948473', constants.ctx, '0')">magnesium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />&nbsp;1.) reflux; 2.) 20 deg C then 22 deg C;&nbsp;<br /> &nbsp;

Stage #1: &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, '1696894', constants.ctx, '0')">diethyl ether</a> <br />T=-15 - 20&deg;C;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4371014', constants.ctx, '0')">ammonium chloride</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, '1696894', constants.ctx, '0')">diethyl ether</a> <br />&nbsp;Inert atmosphere;&nbsp;<br /> &nbsp;