تفاعل #1168918

معادلة التفاعل

methyl iodide

5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine

sodium hydride

water

→

desired product

المردود 35.9%

5-[3-(methoxy)propylthio]imidazo[1,2-a]pyridine

المردود 35.9%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   workup.STIRRINGthe mixture was further stirred under ice-
3. 3
   درجة الحرارةcooling for 30 minutes
4. 4
   workup.STIRRINGby stirring at room temperature overnight
5. 5
   استخلاصwas extracted with methylene chloride (30 ml×3)
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONAfter the solvent was distilled off
8. 8
   أخرىthe residue was purified by column chromatography (eluent:ethyl acetate)

الإجراء التجريبي

To a solution of 5-[3-(hydroxy)propylthio]imidazo[1,2-a]pyridine (803 mg, 3.86 mmoles) in tetrahydrofuran (30 ml) was added 60% sodium hydride in oil (0.19 g, 4.6 mmoles) with stirring under ice-cooling and the mixture was further stirred under ice-cooling for 30 minutes. To the reaction mixture was added methyl iodide (0.36 ml, 5.8 mmoles), followed by stirring at room temperature overnight. The reaction mixture was poured into water, which was extracted with methylene chloride (30 ml×3). The methylene chloride layers were combined and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent:ethyl acetate) to obtain 308 mg of the desired product (35.9%, light brown oily product).

المصدر