Réaction #48709

Équation de réaction

sodium borohydride

2-ethyl benzaldehyde

nitromethane

ammonium acetate

→

desired compound

1-Ethyl-2-(2-nitroethyl)-benzene

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   Températureheat
2. 2
   Températureto reflux under a nitrogen atmosphere for 17 hours
3. 3
   Concentrationconcentrate
4. 4
   workup.DISSOLUTIONDissolve in isopropyl alcohol (150 mL)
5. 5
   workup.ADDITIONchloroform (750 mL) and add silica gel (108 g)
6. 6
   Filtrationfilter
7. 7
   Concentrationconcentrate
8. 8
   Autrepurify
9. 9
   Lavage(silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes)

Mode opératoire

Dissolve 2-ethyl benzaldehyde (7 mL, 53.2 mmol), nitromethane (8.5 mL, 158 mmol), and ammonium acetate (1.6 g, 20.8 mmol) in acetic acid (40 mL) and heat to reflux under a nitrogen atmosphere for 17 hours. Cool to room temperature and concentrate. Dissolve in isopropyl alcohol (150 mL) and chloroform (750 mL) and add silica gel (108 g). To the resulting slurry, slowly add sodium borohydride (7.8 g, 206 mmol). Stir the mixture for 17 hours, filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes), to give the desired compound as an orange oil.

Source