Reaktion #74186

Reaktionsgleichung

4-chlorobicyclo[3.2.1]oct-3-en-2-one

1-[2-(4-chlorophenyl)thiazol-5-yl]ethanol

sodium hydride

→

4-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}bicyclo[3.2.1]oct-3-en-2-one

Ausbeute 74.9%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture is stirred at room temperature overnight
2. 2
   workup.ADDITIONSilica gel is added to the crude
3. 3
   Sonstigereaction mixture
4. 4
   Sonstigethe solvent is evaporated under reduced pressure
5. 5
   Sonstigethe residue is purified by flash chromatography on silica gel

Vorschrift

To a solution of 1-[2-(4-chlorophenyl)thiazol-5-yl]ethanol (1.1 g, 4.6 mmol) in anhydrous tetrahydrofuran (20 ml) is added, in one portion, sodium hydride (60% dispersion in mineral oil, 184 mg, 4.6 mmol). The reaction mixture is stirred for 5 minutes at room temperature and 4-chlorobicyclo[3.2.1]oct-3-en-2-one (720 mg, 4.6 mmol) is added in one portion. The reaction mixture is stirred at room temperature overnight. Silica gel is added to the crude reaction mixture, the solvent is evaporated under reduced pressure and the residue is purified by flash chromatography on silica gel to give 4-{1-[2-(4-chlorophenyl)thiazol-5-yl]ethoxy}bicyclo[3.2.1]oct-3-en-2-one (1.24 g)

Quelle