1: 84 percent / propan-2-ol / 80 °C 2: H2, AcOH / 10percent Pd/C / methanol; tetrahydrofuran View Scheme

1: propan-2-ol / 12 h / 80 °C 2: aq. NaHCO3 3: H2 / 10percent Pd/C / ethyl acetate View Scheme

1.1: isopropyl alcohol / 5 h / 50 °C 2.1: triethylamine / dichloromethane / 12.5 h / 0 - 20 °C 3.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 25 °C 3.2: 29 h 4.1: triethylamine / dichloromethane / 2 h / 25 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3592982', constants.ctx, '0')">sodium methylate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '507772', constants.ctx, '0')">2-chloro-1,1-dimethyl-2-oxoethyl acetate</a> <br />&nbsp;1.) CHCl₃, 23 deg C, 4 h, 2.) THF, 23 deg C, 6 h;&nbsp;&nbsp;Yield given. Multistep reaction;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 87 percent / Ti(OiPr)4; tBuOOH; D-(-)-diethyl tartrate / CH₂Cl₂ / 24 h / -20 &deg;C<br />2: 95 percent / Ti(OiPr)2(N₃)2 / benzene / 0.5 h / Heating<br />3: 92 percent / DMAP; pyridine / 2 h / 0 &deg;C<br />4: 76 percent / NaH / dimethylformamide / 1 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 81 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 &deg;C<br />2: 87 percent / Ti(OiPr)4; tBuOOH; D-(-)-diethyl tartrate / CH₂Cl₂ / 24 h / -20 &deg;C<br />3: 95 percent / Ti(OiPr)2(N₃)2 / benzene / 0.5 h / Heating<br />4: 92 percent / DMAP; pyridine / 2 h / 0 &deg;C<br />5: 76 percent / NaH / dimethylformamide / 1 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 2.7 g / titanium tetraisopropoxide, azidotrimethylsilane / benzene / 0.25 h / Heating<br />2: 1.) 2-acetoxyisobutyryl chloride, 2.) NaOMe / 1.) chloroform, RT, 5 h, 2.) THF, RT, 3 h<br /> <br /> &nbsp;