Reaktion #86798

Reaktionsgleichung

dichloromethane

triethylamine

ethyl 2-chloro-2-(hydroxyimino)acetate

water

→

ethyl 5-chloroisoxazole-3-carboxylate

Ausbeute 39.0%

Lösungsmittel

1,1-dichloroethene

1,1-dichloroethene

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous were extracted with dichloromethane
2. 2
   Sonstigethe organic layers rejoined were dried
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   Sonstigethe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Vorschrift

A mixture of triethylamine (13.12 mL; 90.73 mmol) in 1,1-dichloroethene (75 mL) was added to ethyl 2-chloro-2-(hydroxyimino)acetate (5.5 g; 36.29 mmol) in 1,1-dichloroethene (50 mL) over a period of 2 h the reaction mixture was stirred at room temperature for 20 min and portioned between water (75 mL) and dichloromethane (75 mL). The aqueous were extracted with dichloromethane, the organic layers rejoined were dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford ethyl 5-chloroisoxazole-3-carboxylate 2.5 g (39%).

Quelle