sodium periodate; acetic acid in water

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11343078', constants.ctx, '0')">sodium tetrahydroborate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '506008', constants.ctx, '0')">dimethyl sulfoxide</a> <br />T=85&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 91 percent / DMAP / CH₂Cl₂ / 18 h / 0 - 5 &deg;C<br />2: 80 percent / NaBH₄ / dimethylsulfoxide / 2 h / 85 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 97 percent / PPTS / CH₂Cl₂ / Ambient temperature<br />2: 99 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature<br />3: 91 percent / DMAP / CH₂Cl₂ / 18 h / 0 - 5 &deg;C<br />4: 80 percent / NaBH₄ / dimethylsulfoxide / 2 h / 85 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 68 percent / toluene / 39 h / 0 - 3 &deg;C<br />2: 1.) Mg / 1.) Et₂O, overnight, 2.) Et₂O, 30 min<br />3: 97 percent / PPTS / CH₂Cl₂ / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: NaI, CaCO₃ / tetrahydrofuran<br />2: 1.) Mg / 1.) Et₂O, 1 h, 2.) Et₂O, 30 min<br />3: 97 percent / PPTS / CH₂Cl₂ / Ambient temperature<br />4: 99 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature<br />5: 91 percent / DMAP / CH₂Cl₂ / 18 h / 0 - 5 &deg;C<br />6: 80 percent / NaBH₄ / dimethylsulfoxide / 2 h / 85 &deg;C<br /> <br /> &nbsp;