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

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].

1. temperaturewas refluxed for 20 h
2. customto reach room temperature
3. customThe volume of the reaction was reduced to approx. ⅓, by rotatory evaporation
4. additionthe resulting solution was poured into water (15 mL)
5. extractionextracted with AcOEt (2×15 mL)
6. washThe organic layers were washed with brine (20 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. customAfter removal of the solvent
10. customthe residual brown oil was purified by column chromatography on silica gel (15-30% EtOAc/Hexanes)

ORD record

ord-1a53cec2ddf84430ab44e8d00bb3eca0

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149447B2