1.1: aq. K2CO3 / acetonitrile / 0.5 h / 20 °C 1.2: aq. NaBH4 / acetonitrile / 1 h / 20 °C 2.1: 81 percent / 4 Angstroem molecular sieves; Celite; PCC / CH2Cl2 / 3 h / 20 °C 3.1: 96 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C 4.1: 93 percent / H2 / Pd/Al2O3 / tetrahydrofuran / 4 h / 20 °C / 37503 Torr View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: 87 percent / DIBALH; ZnBr₂ / tetrahydrofuran; heptane / 0.5 h / -78 &deg;C<br />2: 93 percent / AlMe₃ / CH₂Cl₂ / 4 h / Heating<br />3: 71 percent / tetrahydrofuran; diethyl ether / 50 &deg;C<br />4: 92 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.25 h / 0 &deg;C<br />5: TFAA; 2,4,6-collidine / acetonitrile / 0.17 h / 0 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '107283', constants.ctx, '0')">2,4,6-trimethyl-pyridine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '746197', constants.ctx, '0')">trifluoroacetic anhydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />T=0&deg;C;&nbsp;Pummerer reaction;&nbsp;0.166667&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: LDA / tetrahydrofuran / 2 h / -78 &deg;C<br />2: K₂CO₃ / acetone / 2 h / Heating<br />3: 87 percent / DIBALH; ZnBr₂ / tetrahydrofuran; heptane / 0.5 h / -78 &deg;C<br />4: 93 percent / AlMe₃ / CH₂Cl₂ / 4 h / Heating<br />5: 71 percent / tetrahydrofuran; diethyl ether / 50 &deg;C<br />6: 92 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.25 h / 0 &deg;C<br />7: TFAA; 2,4,6-collidine / acetonitrile / 0.17 h / 0 &deg;C<br /> <br /> &nbsp;