反応 #344825

反応方程式

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

収率 66.3%

溶媒

ethyl acetate

HCl

反応条件

後処理

1. 1
   温度the mixture was cooled
2. 2
   workup.STIRRINGthe mixture stirred for 2 hours
3. 3
   その他The 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
   その他the organic layer was separated
7. 7
   洗浄washed with water and saturated sodium chloride solution
8. 8
   乾燥dried over sodium sulfate
9. 9
   濃縮concentrated in vacuo
10. 10
    その他The residue was chromatographed on a column of silica gel using
11. 11
    workup.ADDITIONa mixture of chloroform and methanol (10:1) as eluent

実験手順

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.

出典