تفاعل #84860

معادلة التفاعل

4-(4-(2-(5-(4-bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-(1-ethoxyethoxy)-1-methoxyethyl)phenyl)morpholine

pyridinium para-toluenesulfonate

→

1-(5-(4-bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-methoxy-2-(4-morpholinophenyl)ethanol

المردود 79.0%

المذيبات

MeOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was then heated at 40° C. for 6 hrs
2. 2
   درجة الحرارةcooled to room temp
3. 3
   تركيزconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
5. 5
   غسيلwashed with H2O, saturated NaHCO3 and brine
6. 6
   تجفيفthen dried over Na2SO4
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىPurification by chromatography (50-60% EtOAc-hexanes)

الإجراء التجريبي

To a solution of 4-(4-(2-(5-(4-bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-(1-ethoxyethoxy)-1-methoxyethyl)phenyl)morpholine (0.335 g, 0.57 mmol) in MeOH (15 mL) was added pyridinium para-toluenesulfonate (0.15 g, 0.6 mmol) and the mixture was stirred at room temperature for 16.5 hrs. The reaction was then heated at 40° C. for 6 hrs, cooled to room temp, and concentrated in vacuo. The residue was dissolved in EtOAc and washed with H2O, saturated NaHCO3 and brine then dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (50-60% EtOAc-hexanes) gave 1-(5-(4-bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-methoxy-2-(4-morpholinophenyl)ethanol as a colorless residue (0.234, 79% yield).

المصدر