Reacción #48623

Ecuación de reacción

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

18-Crown-6

potassium fluoride

acetic anhydride

→

desired compound

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

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaCool in an ice bath
2. 2
   workup.STIRRINGstir for 15 minutes
3. 3
   OtroDecant
4. 4
   Extracciónextract the aqueous with ethyl acetate (twice)
5. 5
   LavadoCombine extracts with the solid, wash with water (twice), saturated aqueous sodium chloride (twice),
6. 6
   Secadodry (magnesium sulfate)
7. 7
   Filtraciónfilter
8. 8
   Concentraciónconcentrate
9. 9
   Otropurify
10. 10
    Lavado(silica gel chromatography, eluting with 25:75 hexanes:dichloromethane to 100% dichloromethane)

Procedimiento

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%).

Fuente