Реакция #74181

Уравнение реакции

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

[2-(4-chlorophenyl)selenazol-5-yl]methanol

sodium hydride

→

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

Выход 63.7%

Растворители

tetrahydrofuran

Условия реакции

Обработка

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

Методика

To a solution of [2-(4-chlorophenyl)selenazol-5-yl]methanol (300 mg, 1.1 mmol) in dry tetrahydrofuran (5 ml) is added, in one portion, sodium hydride (60% dispersion in mineral oil, 44 mg, 1.1 mmol). The reaction mixture is stirred for 5 minutes at room temperature and 4-chlorobicyclo[3.2.1]oct-3-en-2-one (172 mg, 1.1 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-[2-(4-chlorophenyl)selenazol-5-ylmethoxy]bicyclo[3.2.1]oct-3-en-2-one (275 mg).

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