تفاعل #344825

معادلة التفاعل

2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetonitrile

tri-n-butyltin azide

→

5-[[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]methyl]-1H-tetrazole

المردود 66.3%

المذيبات

ethyl acetate

HCl

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was cooled
2. 2
   workup.STIRRINGthe mixture stirred for 2 hours
3. 3
   أخرىThe aqueous phase was removed
4. 4
   workup.ADDITIONthe organic phase added to 0.1M potassium fluoride solution
5. 5
   workup.STIRRINGAfter stirring overnight
6. 6
   أخرىthe organic layer was separated
7. 7
   غسيلwashed with water and saturated sodium chloride solution
8. 8
   تجفيفdried over sodium sulfate
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىThe residue was chromatographed on a column of silica gel using
11. 11
    workup.ADDITIONa mixture of chloroform and methanol (10:1) as eluent

الإجراء التجريبي

A mixture of 2-[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetonitrile (1.60 g, 4.2 mmol) and tri-n-butyltin azide (1.45 g, 4.4 mmol) was stirred at 140° C. under an atomosphere of nitrogen. After 20 hours, the mixture was cooled, diluted with ethyl acetate (300 mL) and 1N HCl (200 mL) and the mixture stirred for 2 hours. The aqueous phase was removed and the organic phase added to 0.1M potassium fluoride solution. After stirring overnight, the organic layer was separated, washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on a column of silica gel using a mixture of chloroform and methanol (10:1) as eluent to give 5-[[3-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]methyl]-1H-tetrazole (1.18 g, 66%) after recrystallization from a mixture of hexanes and CH2Cl2 m.p. 138.5°-140° C.

المصدر