Reaktion #55540

Reaktionsgleichung

Allyl bromide

ethyl 2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate

N,N-dimethylformamide

potassium carbonate

→

ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate

Ausbeute 86.4%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe solution was extracted with diethyl ether twice
2. 2
   WaschenThe extract was washed with a saturated aqueous solution of sodium chloride
3. 3
   Trocknendried over magnesium sulfate
4. 4
   EinengenThe solution was concentrated in vacuo
5. 5
   Sonstigethe residue was triturated with a solution of n-hexane and diethyl ether
6. 6
   FiltrationThe precipitates were collected by filtration

Vorschrift

Allyl bromide (2.91 g) was added dropwise to a stirred suspension of ethyl 2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate (syn isomer, 10 g), N,N-dimethylformamide (100 ml) and potassium carbonate (4.54 g) under ice cooling over 5 minutes, and stirred at the same temperature for 4 hours. After adding water (200 ml) to the resultant solution, the solution was extracted with diethyl ether twice. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo, and the residue was triturated with a solution of n-hexane and diethyl ether. The precipitates were collected by filtration to give ethyl 2-(2-tritylaminothiazol-4-yl)-2-allyloxyiminoacetate (syn isomer, 9.4 g), mp. 130° to 132° C.

Quelle