Nitromethane → 1-(Benzyloxy)-3,5-di-tert-butyl-2-[2-nitrovinyl]benzene

Participants

Reaction Steps

To a mixture of 1.5 g (4.6 mmol) of the product of Step A and 2.0 g of ammonium acetate in 25 mL acetic acid was added 3 mL nitromethane. The reaction mixture was refluxed for 5 h, then cooled to room temperature and the volatiles were removed in vacuo. The residue was partitioned between EtOAc and water, then separated. The aqueous layer was re-extracted with EtOAc, the organic layers were combined, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted with 0-20% CH2Cl2-hexane. Combination of the purified fractions and drying in vacuo afforded the title compound.

Provenance & Evidence