Reacción #70239

Ecuación de reacción

3′-fluoro-4′-hydroxyacetophenone

O-(4-nitrobenzyl)hydroxylamine hydrochloride

pyridine

→

3′-fluoro-4′-hydroxyacetophenone-O-4-nitrobenzyloxime

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe solution was concentrated to a pale yellow oil which
2. 2
   workup.ADDITIONwas diluted with dichloromethane/water
3. 3
   ExtracciónThe resultant mixture was extracted with dichloromethane (×3)
4. 4
   LavadoThe combined organic phases were washed with water and brine
5. 5
   Secadodried over magnesium sulphate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated to an off-white solid
8. 8
   OtroThe crude product was purified by column chromatography (SiO2)
9. 9
   Lavadoeluting with 8:2 petrol/ethyl acetate

Procedimiento

A solution of 3′-fluoro-4′-hydroxyacetophenone (0.063 g, 0.411 mmol), O-(4-nitrobenzyl)hydroxylamine hydrochloride (0.100 g, 0.491 mmol) and pyridine (0.13 ml, 1.61 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 5h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with dichloromethane/water. The resultant mixture was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to an off-white solid. The crude product was purified by column chromatography (SiO2), eluting with 8:2 petrol/ethyl acetate, to give a 3′-fluoro-4′-hydroxyacetophenone-O-4-nitrobenzyloxime (CP9-132) as light yellow solid (0.081 g, 65%),

Fuente