Réaction #1857583

Équation de réaction

3-chloro-2-vinylphenol

potassium hydrogencarbonate

tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

N-chlorosuccinimide

→

tert-Butyl 4-{4-[5-(2-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

Solvants

ethyl acetate

water

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 30 min
2. 2
   workup.STIRRINGAfter stirring at room temperature overnight
3. 3
   Extractionextracted with ethyl acetate
4. 4
   SéchageThe organic extracts were dried over sodium sulphate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutreThe residue was purified by chromatography

Mode opératoire

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (400 mg) in ethyl acetate (10 ml) was added N-chlorosuccinimide (206 mg). The reaction mixture is stirred at reflux for 30 min. To the reaction mixture were added 3-chloro-2-vinylphenol (397 mg) and potassium hydrogencarbonate (257 mg) at room temperature, and then one drop of water. After stirring at room temperature overnight, the reaction mixture was admixed with ethyl acetate and water and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-{4-[5-(2-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (345 mg).

Source