Reaktion #700038

Reaktionsgleichung

diethyl azodicarboxylate

Triphenylphosphine

3-Hydroxy-5-phenylisoxazole

2-(N-tert-butoxycarbonylamino)ethanol

→

title compound

Ausbeute 69.5%

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-5-phenylisoxazole

Ausbeute 69.5%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture was stirred at the same temperature for 10 minutes
3. 3
   workup.STIRRINGthe resulting mixture was stirred under ice-
4. 4
   SonstigeThe solvent was evaporated under reduced pressure
5. 5
   Sonstigethe residue was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate=4/1)
6. 6
   Sonstigewas crystallized from isopropyl ether

Vorschrift

Triphenylphosphine (0.87 g) was dissolved in tetrahydrofuran (10 ml), and diethyl azodicarboxylate (0.57 g) was added dropwise to the solution under ice-cooling with stirring, and the mixture was stirred at the same temperature for 10 minutes. 3-Hydroxy-5-phenylisoxazole (0.48 g) and 2-(N-tert-butoxycarbonylamino)ethanol (0.48 g) were added to the reaction mixture, and the resulting mixture was stirred under ice-cooling for 10 minutes and at room temperature for 24 hours. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: cyclohexane/ethyl acetate=4/1) and was crystallized from isopropyl ether to obtain the title compound (0.63 g, 69%) as colorless crystals.

Quelle