trifluoroacetic acid T=0°C; 0.166667 h;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '13159932', constants.ctx, '0')">samarium diiodide</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, '1098229', constants.ctx, '0')">methanol</a> <br />T=0 - 20&deg;C;&nbsp;2&nbsp;h;&nbsp;<br /> &nbsp;

Stage #1: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587218', constants.ctx, '0')">oxygen</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, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78&deg;C;&nbsp;dealkylation;&nbsp;0.25&nbsp;h;&nbsp;<br />Stage #2: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696847', constants.ctx, '0')">dimethylsulfide</a>;&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, '1730733', constants.ctx, '0')">hexane</a> <br />T=20&deg;C;&nbsp;dealkylation;&nbsp;1&nbsp;h;&nbsp;&nbsp;Further stages.;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 19 steps<br /> </b>1.1: O₂; Rose Bengal / acetone / 8 h / -10 &deg;C / Irradiation<br />1.2: RuCl₂(PPh₃)3 / CH₂Cl₂ / -10 - 20 &deg;C<br />1.3: 42 percent / NaOMe / methanol / 0.5 h / -5 &deg;C<br />2.1: 99 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 0 - 20 &deg;C<br />3.1: 80 percent Turnov_. / cholesterol esterase; aq. NaOH / 36 h / 5 &deg;C / pH 7.7<br />4.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 &deg;C<br />5.1: 81 percent Turnov_. / LiOH*H₂O / methanol / 48 h / -5 &deg;C<br />6.1: diphenylphosphorazidate; Et₃N / benzene / 1 h<br />6.2: toluene / 1 h / 110 &deg;C<br />7.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 &deg;C<br />7.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 &deg;C<br />8.1: NaH / dimethylformamide / 0.5 h / -5 &deg;C<br />8.2: dimethylformamide / 0.25 h / -5 &deg;C<br />9.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 &deg;C<br />10.1: 30 percent / benzene / 48 h / 5 &deg;C / UV-irradiation<br />11.1: NaBH₄ / ethanol / 16 h / 20 &deg;C<br />12.1: 12.9 mg / aq. H₂O₂ / tetrahydrofuran; ethanol / 22 h / 20 &deg;C<br />13.1: NaH / tetrahydrofuran / 0.33 h / 20 &deg;C<br />13.2: 94 percent / tetrahydrofuran / 20 h / 20 &deg;C<br />14.1: pyridine; trimethylamine-N-oxide dihydrate; H₂O / OsO₄; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 &deg;C<br />15.1: 19.2 mg / p-TsOH / 2 h / 20 &deg;C<br />16.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 &deg;C<br />17.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating<br />18.1: 3.3 mg / K₂CO₃; H₂O / methanol / 20 &deg;C<br />19.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 &deg;C<br />19.2: 45 percent / NH₄Cl; H₂O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 14 steps<br /> </b>1.1: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h<br />2.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 &deg;C<br />2.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 &deg;C<br />3.1: NaH / dimethylformamide / 0.5 h / -5 &deg;C<br />3.2: dimethylformamide / 0.25 h / -5 &deg;C<br />4.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 &deg;C<br />5.1: 30 percent / benzene / 48 h / 5 &deg;C / UV-irradiation<br />6.1: NaBH₄ / ethanol / 16 h / 20 &deg;C<br />7.1: 12.9 mg / aq. H₂O₂ / tetrahydrofuran; ethanol / 22 h / 20 &deg;C<br />8.1: NaH / tetrahydrofuran / 0.33 h / 20 &deg;C<br />8.2: 94 percent / tetrahydrofuran / 20 h / 20 &deg;C<br />9.1: pyridine; trimethylamine-N-oxide dihydrate; H₂O / OsO₄; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 &deg;C<br />10.1: 19.2 mg / p-TsOH / 2 h / 20 &deg;C<br />11.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 &deg;C<br />12.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating<br />13.1: 3.3 mg / K₂CO₃; H₂O / methanol / 20 &deg;C<br />14.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 &deg;C<br />14.2: 45 percent / NH₄Cl; H₂O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 16 steps<br /> </b>1.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 &deg;C<br />2.1: 81 percent Turnov_. / LiOH*H₂O / methanol / 48 h / -5 &deg;C<br />3.1: diphenylphosphorazidate; Et₃N / benzene / 1 h<br />3.2: toluene / 1 h / 110 &deg;C<br />4.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 &deg;C<br />4.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 &deg;C<br />5.1: NaH / dimethylformamide / 0.5 h / -5 &deg;C<br />5.2: dimethylformamide / 0.25 h / -5 &deg;C<br />6.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 &deg;C<br />7.1: 30 percent / benzene / 48 h / 5 &deg;C / UV-irradiation<br />8.1: NaBH₄ / ethanol / 16 h / 20 &deg;C<br />9.1: 12.9 mg / aq. H₂O₂ / tetrahydrofuran; ethanol / 22 h / 20 &deg;C<br />10.1: NaH / tetrahydrofuran / 0.33 h / 20 &deg;C<br />10.2: 94 percent / tetrahydrofuran / 20 h / 20 &deg;C<br />11.1: pyridine; trimethylamine-N-oxide dihydrate; H₂O / OsO₄; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 &deg;C<br />12.1: 19.2 mg / p-TsOH / 2 h / 20 &deg;C<br />13.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 &deg;C<br />14.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating<br />15.1: 3.3 mg / K₂CO₃; H₂O / methanol / 20 &deg;C<br />16.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 &deg;C<br />16.2: 45 percent / NH₄Cl; H₂O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 13 steps<br /> </b>1.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 &deg;C<br />1.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 &deg;C<br />2.1: NaH / dimethylformamide / 0.5 h / -5 &deg;C<br />2.2: dimethylformamide / 0.25 h / -5 &deg;C<br />3.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 &deg;C<br />4.1: 30 percent / benzene / 48 h / 5 &deg;C / UV-irradiation<br />5.1: NaBH₄ / ethanol / 16 h / 20 &deg;C<br />6.1: 12.9 mg / aq. H₂O₂ / tetrahydrofuran; ethanol / 22 h / 20 &deg;C<br />7.1: NaH / tetrahydrofuran / 0.33 h / 20 &deg;C<br />7.2: 94 percent / tetrahydrofuran / 20 h / 20 &deg;C<br />8.1: pyridine; trimethylamine-N-oxide dihydrate; H₂O / OsO₄; acetone / 2-methyl-propan-2-ol; tetrahydrofuran / 15 h / 20 &deg;C<br />9.1: 19.2 mg / p-TsOH / 2 h / 20 &deg;C<br />10.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 0 &deg;C<br />11.1: 7.1 mg / Burgess reagent / benzene / 16 h / Heating<br />12.1: 3.3 mg / K₂CO₃; H₂O / methanol / 20 &deg;C<br />13.1: n-BuLi; oxygen / tetrahydrofuran; hexane / 0.25 h / -78 &deg;C<br />13.2: 45 percent / NH₄Cl; H₂O; dimethylsulfide / tetrahydrofuran; hexane / 1 h / 20 &deg;C<br /> <br /> &nbsp;