Reaktion #86940

Reaktionsgleichung

1,8-Diazabicyclo[5.4.0]undec-7-ene

ethyl glyoxalate

tosylmethyl isocyanide

→

ethyl oxazole-5-carboxylate

Ausbeute 54.0%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with sodium hydrogen sulphate, sodium carbonate
2. 2
   Trocknendried over magnesium sulphate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe crude mixture was purified by flash chromatography on silica (eluent 5 to 60% ethyl acetate in heptane)

Vorschrift

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.574 mL; 3.84 mmol) was added simultaneously with ethyl glyoxalate (50% in toluene, 0.659 mL; 3.33 mmol) to a mixture of tosylmethyl isocyanide (0.500 g; 2.560 mmol) in dichloromethane (10 mL) at 0° C. The resulting mixture was stirred at room temperature for 3 hours, diluted in dichloromethane and washed with sodium hydrogen sulphate, sodium carbonate, dried over magnesium sulphate and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 5 to 60% ethyl acetate in heptane) to yield 0.194 g (54%) of ethyl oxazole-5-carboxylate as a colorless oil.

Quelle