Réaction #69942

Équation de réaction

5-chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

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

sodium hydride

→

5-[2-(4-chloro-phenyl)-selenazol-5-ylmethoxy]-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Rendement 77.8%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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 5-chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (203 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 5-[2-(4-chloro-phenyl)-selenazol-5-ylmethoxy]-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (360 mg).

Source