تفاعل #69951

معادلة التفاعل

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

المردود 73.2%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىThe crude reaction mixture
2. 2
   workup.ADDITIONare added
3. 3
   درجة الحرارةThe reaction mixture is therefore heated
4. 4
   درجة الحرارةto reflux for 30 minutes
5. 5
   أخرىThe crude reaction mixture
6. 6
   أخرىpurified by flash chromatography on silica gel
7. 7
   أخرىto give a yellow solid
8. 8
   غسيلThe solid is washed with iso-hexane

الإجراء التجريبي

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).

المصدر