Реакция #74182

Уравнение реакции

(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

Выход 81.9%

Растворители

tetrahydrofuran

Условия реакции

Обработка

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

Методика

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)

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