1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 89 percent / TsOH*H2O / 5 h / 60 °C 3: 92 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 92 percent / KOH / methanol / 3 h / Ambient temperature 8: 86 percent / propan-2-ol / 6 h / 80 °C 9: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h View Scheme

1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 89 percent / TsOH*H2O / 5 h / 60 °C 3: 92 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 92 percent / KOH / methanol / 3 h / Ambient temperature 8: 86 percent / propan-2-ol / 6 h / 80 °C 9: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h 10: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature 11: H2 / 10percent Pd/C / ethanol / 16 h 12: 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 16 h / Ambient temperature View Scheme

1: NaBH4 / ethanol / 1 h / -15 - -10 °C 2: 89 percent / TsOH*H2O / 5 h / 60 °C 3: 92 percent / 1 M aq. NaOH / ethanol / 18 h / Ambient temperature 4: (COCl)2, DMF / toluene / 1 h 5: CBrCl3, 2-mercaptopyridine N-oxide sodium salt, 4-(dimethylamino)pyridine / 1 h / 80 °C / Irradiation 6: aq. AcOH, conc. HCl / 3 h / Ambient temperature 7: 92 percent / KOH / methanol / 3 h / Ambient temperature 8: 86 percent / propan-2-ol / 6 h / 80 °C 9: 100 percent / H2 / 10percent Pd/C / ethanol / 24 h 10: 48 percent / 1-hydroxybenzotriazole hydrate, dicyclohexylcarbodiimide, N-ethylmorpholine / tetrahydrofuran / 64 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '8973685', constants.ctx, '0')">zinc</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />1&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 84 percent / Et₃N, SOCl₂ / benzene / 3 h / 5 &deg;C<br />2: 64 percent / Zn / tetrahydrofuran / 1 h / Heating<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '6826', constants.ctx, '0')">1,1'-carbonyldiimidazole</a> <br />&nbsp;Multistep reaction;&nbsp;<br /> &nbsp;