1: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 2: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating 5: hydrochloric acid / ethanol View Scheme

1: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 2: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C View Scheme

1: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 2: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating View Scheme

1: 93 percent / potassium carbonate / methanol / 2 h / 22 °C 2: 81 percent / 2 M oxalyl chloride, dimethyl sulfoxide, triethylamine / CH2Cl2 / -60 °C 3: 1) sodium methylsulfinylmethide / 1) dimethyl sulfoxide, tetrahydrofuran, 0 deg C, 2 min, 2) tetrahydrofuran, 0 deg C, 30 min, then 24 deg C, 1 h 4: hexane; methanol / 14 h / Heating 5: hydrochloric acid / ethanol 6: 93 percent / hydrogen / 5 percent palladium on carbon / ethanol / 0.25 h / 775.7 Torr View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1099903', constants.ctx, '0')">N,N,N',N',N'',N''-hexamethylphosphoric triamide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '4152656', constants.ctx, '0')">sodium cyanoborohydride</a> <br />T=70&deg;C;&nbsp;10&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1: 84 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0 deg C to 22 deg C, 22 h<br />2: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 &deg;C<br />3: 96 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 8 h / 22 &deg;C<br />4: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl₄ / Heating; Irradiation<br />5: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: 82 percent / N,N-dimethylaniline / 2.5 h / 193 &deg;C<br />2: 84 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0 deg C to 22 deg C, 22 h<br />3: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 &deg;C<br />4: 96 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 8 h / 22 &deg;C<br />5: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl₄ / Heating; Irradiation<br />6: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 &deg;C<br />2: 96 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 8 h / 22 &deg;C<br />3: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl₄ / Heating; Irradiation<br />4: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 7 steps<br /> </b>1: 1) potassium tert-butoxide / 1) tert-butyl alcohol, reflux, o.5 h, 2) tert-butyl alcohol, reflux, 8 h<br />2: 82 percent / N,N-dimethylaniline / 2.5 h / 193 &deg;C<br />3: 84 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0 deg C to 22 deg C, 22 h<br />4: 75 percent / potassium hydroxide, water / dimethylsulfoxide / 3 h / 23 &deg;C<br />5: 96 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 8 h / 22 &deg;C<br />6: 91 percent / N-bromosuccinimide, benzoylperoxide / CCl₄ / Heating; Irradiation<br />7: sodium cyanoborohydride, hexamethylphosphoramide / 10 h / 70 &deg;C<br /> <br /> &nbsp;