1: 1.) TMSCl, NaI, Dabco, 2.) 6 N aq. HCl / 1.) CH3CN, reflux, 5 h, 2.) 100 deg C, 4 h 2: 95 percent / H2, NaOAc / Pd/C / methanol 3: 87 percent / t-BuOK / 1,2-dimethoxy-ethane / 48 h / Heating 4: 59 percent / Pd(OAc)2, Bu4N(1+)*Br(1-), KOAc / dimethylformamide / 3 h / 90 °C View Scheme

1: 1.) TMSCl, NaI, Dabco, 2.) 6 N aq. HCl / 1.) CH3CN, reflux, 5 h, 2.) 100 deg C, 4 h 2: 95 percent / H2, NaOAc / Pd/C / methanol View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11342940', constants.ctx, '0')">sodium hydroxide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1718733', constants.ctx, '0')">ethanol</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 92 percent / Et₃SIH, TFA<br />2: 1.) n-BuLi<br />3: 76 percent / 2 N aq. NaOH / ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 1.) n-BuLi<br />2: 76 percent / 2 N aq. NaOH / ethanol<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 1.) t-BuLi, 3.) n-BuLi, 4.) I₂ <br />2: 92 percent / Et₃SIH, TFA<br />3: 1.) n-BuLi<br />4: 76 percent / 2 N aq. NaOH / ethanol<br /> <br /> &nbsp;