Reaktion #74182

Reaktionsgleichung

(2-bromothiazol-5-yl)methanol

4-chloro-bicyclo[3.2.1]oct-3-en-2-one

sodium hydride

→

4-(2-bromothiazol-5-ylmethoxy)bicyclo[3.2.1]oct-3-en-2-one

Ausbeute 81.9%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONSilica gel is added to the crude
2. 2
   Sonstigereaction mixture
3. 3
   Sonstigethe solvent is evaporated under reduced pressure
4. 4
   Sonstigethe residue is purified by flash chromatography on silica gel

Vorschrift

To a solution of (2-bromothiazol-5-yl)methanol (4.85 g, 25 mmol) and 4-chloro-bicyclo[3.2.1]oct-3-en-2-one (3.92 g, 25 mmol) in anhydrous tetrahydrofuran (100 ml) is added, in small portions, sodium hydride (60% dispersion in oil, 1.00 g, 25 mmol) at 0° C. The reaction mixture is stirred overnight and allowed to warm to room temperature. 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-(2-bromothiazol-5-ylmethoxy)bicyclo[3.2.1]oct-3-en-2-one (6.43 g)

Quelle