Réaction #48719

Équation de réaction

3-benzyloxy-5-fluoro-benzaldehyde

nitromethane

ammonium acetate

→

desired compound

Rendement 68.5%

1-benzyloxy-3-fluoro-5-((E)-2-nitro-vinyl)-benzene

Rendement 68.5%

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   ExtractionExtract with hexanes/ethyl acetate
2. 2
   SéchageDry (magnesium sulfate)
3. 3
   Filtrationfilter
4. 4
   Concentrationconcentrate
5. 5
   AutrePurify on 120 g silica gel eluting with 100:0 to 80:20 hexanes

Mode opératoire

Heat 3-benzyloxy-5-fluoro-benzaldehyde (3.75 g, 16.29 mmol), nitromethane (4.08 g, 66.79 mmol), and ammonium acetate (3.47 g, 44.96 mmol) in acetic acid (54 mL) in 125° C. oil bath under nitrogen for 4 hours. Cool to room temperature and pour into ice/water. Extract with hexanes/ethyl acetate. Dry (magnesium sulfate), filter and concentrate. Purify on 120 g silica gel eluting with 100:0 to 80:20 hexanes:ethyl acetate to give 3.05 g (68.5%) of the desired compound as a yellow oil.

Source