تفاعل #1833271

معادلة التفاعل

4-((2-methoxyethoxy)methoxy)benzaldehyde

Intermediate I

4-((2-methoxyethoxy)methoxy)benzaldehyde

CH3NO2

→

(E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene

المردود 79.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas refluxed for 20 h
2. 2
   أخرىto reach room temperature
3. 3
   أخرىThe volume of the reaction was reduced to approx. ⅓, by rotatory evaporation
4. 4
   workup.ADDITIONthe resulting solution was poured into water (15 mL)
5. 5
   استخلاصextracted with AcOEt (2×15 mL)
6. 6
   غسيلThe organic layers were washed with brine (20 mL)
7. 7
   تجفيفdried over anhydrous Na2SO4
8. 8
   ترشيحfiltered
9. 9
   أخرىAfter removal of the solvent
10. 10
    أخرىthe residual brown oil was purified by column chromatography on silica gel (15-30% EtOAc/Hexanes)

الإجراء التجريبي

A mixture of 4-((2-methoxyethoxy)methoxy)benzaldehyde (Intermediate I, 1.86 g, 8.85 mmol) and NH4OAc (0.75 g, 9.73 mmol) in dry THF (15 mL) and CH3NO2 (15 mL) was refluxed for 20 h and allowed to reach room temperature. The volume of the reaction was reduced to approx. ⅓, by rotatory evaporation; the resulting solution was poured into water (15 mL) and extracted with AcOEt (2×15 mL). The organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residual brown oil was purified by column chromatography on silica gel (15-30% EtOAc/Hexanes) affording 1.77 g of (E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene [Rf=0.7 (50% AcOEt/Hexanes), yellow solid, 79% yield].

المصدر