Reacción #67990

Ecuación de reacción

tetrahydrofuran

m-anisidine

triethylamine

allyl bromide

→

N-allyl-3-methoxyaniline

Disolventes

ethyl acetate

Water

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente