反応 #48623

反応方程式

3-(1-hydroxy-2-nitroethyl)-phenol

18-Crown-6

potassium fluoride

acetic anhydride

→

desired compound

Acetic acid 3-(2-nitrovinyl)-phenyl ester

溶媒

反応条件

後処理

1. 1
   温度Cool in an ice bath
2. 2
   workup.STIRRINGstir for 15 minutes
3. 3
   その他Decant
4. 4
   抽出extract the aqueous with ethyl acetate (twice)
5. 5
   洗浄Combine extracts with the solid, wash with water (twice), saturated aqueous sodium chloride (twice),
6. 6
   乾燥dry (magnesium sulfate)
7. 7
   ろ過filter
8. 8
   濃縮concentrate
9. 9
   その他purify
10. 10
    洗浄(silica gel chromatography, eluting with 25:75 hexanes:dichloromethane to 100% dichloromethane)

実験手順

Add 3-(1-hydroxy-2-nitroethyl)-phenol (22.3 g, 121.8 mmol), 18-Crown-6 (3.3 g, 12.5 mmol), potassium fluoride (spray-dried) (7.1 g, 141 mmol) to acetic anhydride (115 mL, 1.218 mol). Stir for 1 hour. Cool in an ice bath and pour into ice water (400 mL) and stir for 15 minutes. Decant and extract the aqueous with ethyl acetate (twice). Combine extracts with the solid, wash with water (twice), saturated aqueous sodium chloride (twice), dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 25:75 hexanes:dichloromethane to 100% dichloromethane) to give the desired compound as an orange oil (25.56 g, 91%).

出典