1: LiAlH4, TiCl3 / tetrahydrofuran / 1 h / Ambient temperature 2: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: LiAlH4, TiCl3 / tetrahydrofuran / 1 h / Ambient temperature 2: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 3: MnO2 / CH2Cl2 / 2 h / Ambient temperature 4: 80 percent / AgO, NaCN / methanol / 18 h / Ambient temperature View Scheme

1: LiAlH4, TiCl3 / tetrahydrofuran / 1 h / Ambient temperature 2: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature 3: MnO2 / CH2Cl2 / 2 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11378939', constants.ctx, '0')">Lindlar's catalyst</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 95 percent / imidazole / dimethylformamide / 18 h / Ambient temperature<br />2: H₂ / Lindlar catalyst / methanol / 24 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 95 percent / imidazole / dimethylformamide / 18 h / Ambient temperature<br />2: H₂ / Lindlar catalyst / methanol / 24 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 95 percent<br />2: 90 percent / EtMgBr<br />3: 1.) DIBAL<br />4: 85 percent / Lindlar<br /> <br /> &nbsp;