2: 80 percent / 5percent HCl / tetrahydrofuran / 216 h / 25 °C View Scheme

Yield givenMultistep reaction;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11342938', constants.ctx, '0')">lithium hydroxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</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, '1098229', constants.ctx, '0')">methanol</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a> <br />T=75&deg;C;&nbsp;65&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 1) Me₃Al / 1a) toluene, -6 deg C, 10 min, 1b) 25 deg C, 50 min, 2) toluene, 16h, reflux<br />2: 1) t-BuLi, 2) ICl / 1) ether, pentane, -45 to 40 deg C, 30 min, 2) -78 to 25 deg C<br />3: 2) Na₂CO₃ / 1) CH₂Cl₂, 25 deg C, 7.5h, 2) MeOH, 25 deg C, 12h<br />4: 1) NaH / 1a) THF, 0 deg C, 30 min, 1b) 25 deg C, 2.5h, 2a) 0 deg C, 1.5h, 2b) 25 deg C, 21.5h<br />5: 86 percent / LiOH-H₂O / tetrahydrofuran; methanol; H₂O / 65 h / 75 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 2) Na₂CO₃ / 1) CH₂Cl₂, 25 deg C, 7.5h, 2) MeOH, 25 deg C, 12h<br />2: 1) NaH / 1a) THF, 0 deg C, 30 min, 1b) 25 deg C, 2.5h, 2a) 0 deg C, 1.5h, 2b) 25 deg C, 21.5h<br />3: 86 percent / LiOH-H₂O / tetrahydrofuran; methanol; H₂O / 65 h / 75 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 1) NaH / 1a) THF, 0 deg C, 25 min, 1b) 25 deg C, 30 min, 2) 25 deg C, 12h<br />2: 1) Me₃Al / 1a) toluene, -6 deg C, 10 min, 1b) 25 deg C, 50 min, 2) toluene, 16h, reflux<br />3: 1) t-BuLi, 2) ICl / 1) ether, pentane, -45 to 40 deg C, 30 min, 2) -78 to 25 deg C<br />4: 2) Na₂CO₃ / 1) CH₂Cl₂, 25 deg C, 7.5h, 2) MeOH, 25 deg C, 12h<br />5: 1) NaH / 1a) THF, 0 deg C, 30 min, 1b) 25 deg C, 2.5h, 2a) 0 deg C, 1.5h, 2b) 25 deg C, 21.5h<br />6: 86 percent / LiOH-H₂O / tetrahydrofuran; methanol; H₂O / 65 h / 75 &deg;C<br /> <br /> &nbsp;