Reaktion #74181

Reaktionsgleichung

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

Ausbeute 63.7%

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 [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).

Quelle