1: NaBH4, CeCl3 / methanol / 0.17 h / 20 °C 2: 80percent aq. formic acid / 0.67 h / 80 - 85 °C View Scheme

1.1: trimethyl orthoformate; p-toluenesulfonic acid hydrate; mol. sieves / CH2Cl2 / 15 h / 20 °C 2.1: Li; N,N-dimethyl-1-naphthylamine / tetrahydrofuran / 2 h / -65 °C 2.2: tetrahydrofuran / -65 - 20 °C 2.3: 88 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme

1.1: trimethyl orthoformate; p-toluenesulfonic acid hydrate; mol. sieves / CH2Cl2 / 15 h / 20 °C 2.1: Li; N,N-dimethyl-1-naphthylamine / tetrahydrofuran / 2 h / -65 °C 2.2: tetrahydrofuran / -65 - 20 °C 2.3: 5 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1: Zn(Cu) / diethyl ether / 5 h<br />2: diethyl ether / 1 h / 5 &deg;C<br />3: Li₂CO₃ / dimethylformamide / 0.67 h / 80 &deg;C<br /> <br /> &nbsp;