Reaction #1833271

Reaction equation

4-((2-methoxyethoxy)methoxy)benzaldehyde

Intermediate I

4-((2-methoxyethoxy)methoxy)benzaldehyde

CH3NO2

→

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

Yield 79.0%

Solvents

THF

Conditions

Workup

1. 1
   Temperaturewas refluxed for 20 h
2. 2
   Otherto reach room temperature
3. 3
   OtherThe 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
   Extractionextracted with AcOEt (2×15 mL)
6. 6
   WashThe organic layers were washed with brine (20 mL)
7. 7
   Dryingdried over anhydrous Na2SO4
8. 8
   Filtrationfiltered
9. 9
   OtherAfter removal of the solvent
10. 10
    Otherthe residual brown oil was purified by column chromatography on silica gel (15-30% EtOAc/Hexanes)

Procedure

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].

Source