1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure 2: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C 3: 85 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C View Scheme

1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure 2: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C View Scheme

<b>Multi-step reaction with 4 steps<br /> </b>1.1: 92 percent / imidazole / dimethylformamide / 20 &deg;C<br />2.1: t-BuLi / pentane / 0.5 h / -78 &deg;C<br />2.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 &deg;C<br />3.1: 75 percent / NaBH₃CN; Cl₂CHCO₂H / various solvent(s) / 0.5 h / -25 &deg;C<br />4.1: 67 percent / 450 &deg;C / 0 Torr<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1.1: 96 percent / cesium carbonate / dimethylformamide / 2 h / 50 &deg;C<br />2.1: 91 percent / 2-methyl-2-butene; aq. sodium chlorite; NaH₂PO₄ / 2-methyl-propan-2-ol / 4 h / 20 &deg;C<br />3.1: oxalyl chloride / dimethylformamide; CH₂Cl₂ / 18 h / 20 &deg;C<br />4.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl₃; AIBN / 0.08 h / Heating<br />5.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 &deg;C<br />6.1: 92 percent / imidazole / dimethylformamide / 20 &deg;C<br />7.1: t-BuLi / pentane / 0.5 h / -78 &deg;C<br />7.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 &deg;C<br />8.1: 75 percent / NaBH₃CN; Cl₂CHCO₂H / various solvent(s) / 0.5 h / -25 &deg;C<br />9.1: 67 percent / 450 &deg;C / 0 Torr<br /> <br /> &nbsp;