Réaction #69951

Équation de réaction

triglyme

[2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanol

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

sodium hydride

→

5-{1-[2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Rendement 73.2%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   AutreThe crude reaction mixture
2. 2
   workup.ADDITIONare added
3. 3
   TempératureThe reaction mixture is therefore heated
4. 4
   Températureto reflux for 30 minutes
5. 5
   AutreThe crude reaction mixture
6. 6
   Autrepurified by flash chromatography on silica gel
7. 7
   Autreto give a yellow solid
8. 8
   LavageThe solid is washed with iso-hexane

Mode opératoire

To a solution of [2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethanol (450 mg, 1.5 mmol) and 5-chloro-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (277 mg, 1.5 mmol) in tetrahydrofuran (10 ml) is added in one portion the sodium hydride (60% dispersion in mineral oil, 60 mg, 1.5 mmol). The reaction mixture is stirred at room temperature for 24 hours. The crude reaction mixture is vacced down under reduced pressure and 10 ml of triglyme are added. The reaction mixture is therefore heated to reflux for 30 minutes. The crude reaction mixture is vacced down and purified by flash chromatography on silica gel to give a yellow solid. The solid is washed with iso-hexane to give 5-{1-[2-(4-bromo-2-methyl-phenyl)-thiazol-5-yl]-ethoxy}-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (490 mg).

Source