Réaction #1163868

Équation de réaction

nicotinoyl chloride oxime hydrochloride

1-iodovinylcyclopropane

triethylamine

→

3-(5-Cyclopropyl-3-isoxazolyl)pyridine

Solvants

ethanol

ethanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONTo a stirred mixture containing 1.35 g
2. 2
   Autrethe solvent is removed under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue is dissolved in water
4. 4
   Autreether and the ether layer is separated
5. 5
   ExtractionThe water layer is extracted twice with ether
6. 6
   Séchagethe combined ether layers are dried over sodium sulfate
7. 7
   FiltrationFiltration and removal of the solvent under reduced pressure
8. 8
   Autregives an orange-yellow solid
9. 9
   AutreThis material is recrystallized from isopropyl alcohol
10. 10
    Autreto give white crystals, melting point 74°-75°C., nmr spectrum δ6.82 (DMSO-d6, s, 4-isoxazolyl H)

Mode opératoire

To a stirred mixture containing 1.35 g. of nicotinoyl chloride oxime hydrochloride and 2.6 g. of 1-iodovinylcyclopropane in 50 ml. of ethanol is added dropwise over a 1 hour period, a solution of 4.27 g. of triethylamine in 40 ml. of ethanol. The reaction is stirred for 1 hour and then the solvent is removed under reduced pressure. The residue is dissolved in water and ether and the ether layer is separated. The water layer is extracted twice with ether and then the combined ether layers are dried over sodium sulfate. Filtration and removal of the solvent under reduced pressure gives an orange-yellow solid. This material is recrystallized from isopropyl alcohol to give white crystals, melting point 74°-75°C., nmr spectrum δ6.82 (DMSO-d6, s, 4-isoxazolyl H).

Source