1: 93 percent / TsOH*H2O / benzene / 1 h / Heating 2: 66 percent / O3 / CH2Cl2; methanol / -78 °C 3: 92 percent / LiOH*H2O / methanol; H2O / 1 h / Ambient temperature View Scheme

1: 97 percent / pyridine / 10 h / 20 °C 2: TFA / CH2Cl2 / 1 h / 20 °C 3: tetrahydrofuran / 2.5 h / 20 °C 4: 89 percent / dppp; 1,8-diazabicyclo[5.4.0]undec-7-ene / Pd2(dba)3 / dimethylsulfoxide / 4 h / 50 °C 5: ethylenediamine / 6 h / 160 °C 6: CH2Cl2 / 12 h / 20 °C 7: H2 / Rh(acac)(CO)2; biphephos / tetrahydrofuran / 8 h / 65 °C / 3800 Torr 8: 10-camphorsulfonic acid / tetrahydrofuran / 9 h / 20 °C 9: 100 percent / H2 / palladium on carbon / ethanol / 12 h / 20 °C / 760 Torr 10: 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 20 °C 11: 96 percent / sodium; naphthalene / tetrahydrofuran / 1 h / -78 °C 12: 87 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 18 h / 0 °C 13: 95 percent / trifluoroacetic acid; NaHCO3 / 2 h / 20 °C View Scheme

Stage #1: &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=25 - 30&deg;C;&nbsp;2.5&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4371014', constants.ctx, '0')">ammonium chloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=5 - 20&deg;C;&nbsp;0.25&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 10percent aq. NaOH, 4-(dimethylamino)pyridine / tetrahydrofuran; H₂O; CH₂Cl₂ / 6 h / Heating<br />2: 1.) oxalyl chloride, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, a) -60 deg C to -35 deg C, 20 min, b) -35 deg C, 5 min, 2.) -35 deg C to -5 to 0 deg C, 10 min<br />3: CH₂Cl₂; tetrahydrofuran / 1 h / Ambient temperature<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: 10percent aq. NaOH, 4-(dimethylamino)pyridine / tetrahydrofuran; H₂O; CH₂Cl₂ / 6 h / Heating<br />2: 1.) oxalyl chloride, DMSO, 2.) diisopropylethylamine / 1.) CH₂Cl₂, a) -60 deg C to -35 deg C, 20 min, b) -35 deg C, 5 min, 2.) -35 deg C to -5 to 0 deg C, 10 min<br />3: CH₂Cl₂; tetrahydrofuran / 1 h / Ambient temperature<br /> <br /> &nbsp;