반응 #48623

반응 방정식

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

18-Crown-6

potassium fluoride

acetic anhydride

→

desired compound

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

용매

반응 조건

후처리

1. 1
   온도Cool in an ice bath
2. 2
   workup.STIRRINGstir for 15 minutes
3. 3
   기타Decant
4. 4
   추출extract the aqueous with ethyl acetate (twice)
5. 5
   세척Combine extracts with the solid, wash with water (twice), saturated aqueous sodium chloride (twice),
6. 6
   건조dry (magnesium sulfate)
7. 7
   여과filter
8. 8
   농축concentrate
9. 9
   기타purify
10. 10
    세척(silica gel chromatography, eluting with 25:75 hexanes:dichloromethane to 100% dichloromethane)

실험 절차

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%).

출처