Reaktion #70239

Reaktionsgleichung

3′-fluoro-4′-hydroxyacetophenone

O-(4-nitrobenzyl)hydroxylamine hydrochloride

pyridine

→

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

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe solution was concentrated to a pale yellow oil which
2. 2
   workup.ADDITIONwas diluted with dichloromethane/water
3. 3
   ExtraktionThe resultant mixture was extracted with dichloromethane (×3)
4. 4
   WaschenThe combined organic phases were washed with water and brine
5. 5
   Trocknendried over magnesium sulphate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to an off-white solid
8. 8
   SonstigeThe crude product was purified by column chromatography (SiO2)
9. 9
   Wascheneluting with 8:2 petrol/ethyl acetate

Vorschrift

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%),

Quelle