1: 87 percent / NaH / tetrahydrofuran / 2.5 h 2: 1) NaH, n-BuLi / 1) THF, 0 deg C, 10 min, 2) THF, 0 deg C, 1 h 3: 99 percent / CF3COOH / CHCl3 / 0.67 h / 23 °C 4: 98 percent / LiBr, DMSO / 0.67 h / 180 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3570522', constants.ctx, '0')">tetrabutyl ammonium fluoride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=23&deg;C;&nbsp;0.333333&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 90 percent / diisopropylethyl amine / CH₂Cl₂ / 3.5 h / 23 &deg;C<br />2: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />3: 97 percent / pyridine / a) 0 deg C, 15 min, b) 20 min<br />4: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 97 percent / pyridine / a) 0 deg C, 15 min, b) 20 min<br />2: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />2: 97 percent / pyridine / a) 0 deg C, 15 min, b) 20 min<br />3: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 1) n-BuLi / 1) THF, -76 deg C, 10 min, 2) THF, 1 h<br />2: 90 percent / diisopropylethyl amine / CH₂Cl₂ / 3.5 h / 23 &deg;C<br />3: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />4: 97 percent / pyridine / a) 0 deg C, 15 min, b) 20 min<br />5: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: imidazole / CH₂Cl₂ <br />2: 1) n-BuLi / 1) THF, -76 deg C, 10 min, 2) THF, 1 h<br />3: 90 percent / diisopropylethyl amine / CH₂Cl₂ / 3.5 h / 23 &deg;C<br />4: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 &deg;C<br />5: 97 percent / pyridine / a) 0 deg C, 15 min, b) 20 min<br />6: 98 percent / (n-Bu)4NF / tetrahydrofuran / 0.33 h / 23 &deg;C<br /> <br /> &nbsp;