Reaktion #67990

Reaktionsgleichung

tetrahydrofuran

m-anisidine

triethylamine

allyl bromide

→

N-allyl-3-methoxyaniline

Lösungsmittel

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturunder cooling with ice
3. 3
   SonstigeThe organic layer was separated
4. 4
   Sonstigethe aqueous layer was separated with ethyl acetate
5. 5
   Waschenthe resultant solution was washed with an aqueous saturated sodium chloride solution
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Sonstigethe solvent was removed under reduced pressure
8. 8
   SonstigeThe residue thus obtained
9. 9
   Sonstigewas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Vorschrift

To 10 mL of a tetrahydrofuran solution containing 1.0 g of m-anisidine, 1.2 mL of triethylamine and 0.70 mL of allyl bromide were added under cooling with ice. The reaction mixture was stirred for 30 minutes. Water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was separated with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to obtain 0.36 g of a yellow oily substance, N-allyl-3-methoxyaniline.

Quelle