1: 105 mg / 1,5N KOH/EtOH / 0.17 h / Ambient temperature 2: CuBr*Me2S / diethyl ether / Ambient temperature; or Cu(I)-pentin-1-ide 3: 480 mg / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

1: 105 mg / 1,5N KOH/EtOH / 0.17 h / Ambient temperature 2: CuBr*Me2S / diethyl ether / Ambient temperature; or Cu(I)-pentin-1-ide 3: 480 mg / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 1 h / Ambient temperature 4: 1) H2, 2) conc. HCl / 1) 10percent Pd/C / 1) MeOH, 760 Torr, 2) 50 deg C, 2h View Scheme

<b>Multi-step reaction with 5 steps<br /> </b>1: H₂ / 5percent Pd/C / toluene / 760 Torr<br />2: 50percent NaOH / Bu₄NBr / toluene / Ambient temperature<br />3: KOtBu, BuLi / tetrahydrofuran / 0.5 h / Ambient temperature<br />4: 1) NaH / 1) THF, r.t., 2) THF, pentane, r.t., 16h<br />5: 95 percent / pyridine / CH₂Cl₂ / a) 0 deg C, 1h, b) r.t., 16h<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: SOCl₂, pyridine<br />3: tetrahydrofuran / a) -78 deg C, 5h, b) -20 deg C, 16h<br />4: reducing agent: hydride<br />5: 95 percent / pyridine / CH₂Cl₂ / a) 0 deg C, 1h, b) r.t., 16h<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103233', constants.ctx, '0')">pyridine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />&nbsp;a) 0 deg C, 1h, b) r.t., 16h;&nbsp;<br /> &nbsp;