1: 96 percent / aq. NaOH / methanol; tetrahydrofuran 2: 93 percent / Li, NH3 / tetrahydrofuran / 2 h / -78 °C 3: 1.) PDC, 2.) NaClO2, NaH2PO4 / 1.) 5 h, 2.) 2-methyl-2-butene, t-BuOH, 20 min 4: 96 percent / (n-Bu)4NF / tetrahydrofuran / 13 h / 55 °C View Scheme

1: 96 percent / aq. NaOH / methanol; tetrahydrofuran 2: 93 percent / Li, NH3 / tetrahydrofuran / 2 h / -78 °C 3: 95 percent / (n-Bu)4NF / tetrahydrofuran / 12 h / 55 °C View Scheme

1: 96 percent / aq. NaOH / methanol; tetrahydrofuran 2: 93 percent / Li, NH3 / tetrahydrofuran / 2 h / -78 °C 3: 1.) n-BuLi, ClPO(NMe2)2, 2.) Li, EtNH2 / 1.) THF, HMPA, 2.) THF, t-BuOH, 0 deg C, 3 h 4: 95 percent / (n-Bu)4NF / tetrahydrofuran / 12 h / 55 °C View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1: 56 percent / Et₂Zn / toluene / 8 h / Ambient temperature<br />2: DIBAL / CH₂Cl₂ <br />3: imidazole / dimethylformamide / 10 h / 55 &deg;C<br />4: 61 percent / CuBr / chlorobenzene / 4 h / 115 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: imidazole / dimethylformamide / 10 h / 55 &deg;C<br />2: 61 percent / CuBr / chlorobenzene / 4 h / 115 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 72 percent / Pb(OAc)4, Cu(OAc)2, pyridine / acetonitrile / 80 &deg;C<br />2: 56 percent / Et₂Zn / toluene / 8 h / Ambient temperature<br />3: DIBAL / CH₂Cl₂ <br />4: imidazole / dimethylformamide / 10 h / 55 &deg;C<br />5: 61 percent / CuBr / chlorobenzene / 4 h / 115 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8128144', constants.ctx, '0')">copper(I) bromide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605632', constants.ctx, '0')">chlorobenzene</a> <br />T=115&deg;C;&nbsp;4&nbsp;h;&nbsp;<br /> &nbsp;