ammonia; sodium in tetrahydrofuran T=-78°C; 4 h;

lithium aluminium tetrahydride in diethylene glycol dimethyl ether

1: 82 percent / Na/NH3 / tetrahydrofuran / 4 h / -78 °C 2: 82 percent / pyridine / 1) 0 deg C, 1 h, 2) overnight View Scheme

1: hydrogen / Lindlar catalyst 2: 67 percent / pyridinium chlorochromate View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: LiNH₂, NH₃ (liquid)<br />2: 80 percent / Ph₃P, Br₂ (5.5 M in CCl₄), pyridine / CH₂Cl₂ / 2 h / Ambient temperature<br />3: NaH / 1) DMF, 0-60 deg C, 2) 4 h, 60 deg C<br />4: LiCl*H₂O, H₂O / 4 h / 160 - 165 &deg;C<br />5: 90 percent / LAH / diethyl ether<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: NaH / 1) DMF, 0-60 deg C, 2) 4 h, 60 deg C<br />2: LiCl*H₂O, H₂O / 4 h / 160 - 165 &deg;C<br />3: 90 percent / LAH / diethyl ether<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: LiCl*H₂O, H₂O / 4 h / 160 - 165 &deg;C<br />2: 90 percent / LAH / diethyl ether<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3902898', constants.ctx, '0')">hydrogen cation</a> <br />&nbsp;Yield given;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1.) bromination reagent<br />2: dimethylformamide; liquid ammonia<br />3: BuLi<br />4: H⁽¹⁺⁾ <br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: LiNH₂, NH₃ (liquid)<br />2: 80 percent / Ph₃P, Br₂ (5.5 M in CCl₄), pyridine / CH₂Cl₂ / 2 h / Ambient temperature<br />3: NaH / 1) DMF, 0-60 deg C, 2) 4 h, 60 deg C<br />4: LiCl*H₂O, H₂O / 4 h / 160 - 165 &deg;C<br />5: 90 percent / LAH / diethyl ether<br /> <br /> &nbsp;