反応 #67990

反応方程式

tetrahydrofuran

m-anisidine

triethylamine

allyl bromide

→

N-allyl-3-methoxyaniline

溶媒

ethyl acetate

Water

反応条件

後処理

1. 1
   workup.ADDITIONwere added
2. 2
   温度under cooling with ice
3. 3
   その他The organic layer was separated
4. 4
   その他the aqueous layer was separated with ethyl acetate
5. 5
   洗浄the resultant solution was washed with an aqueous saturated sodium chloride solution
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   その他the solvent was removed under reduced pressure
8. 8
   その他The residue thus obtained
9. 9
   その他was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

実験手順

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.

出典