تفاعل #342009

معادلة التفاعل

diisopropyl azodicarboxylate

5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1H-tetrazole

furfuryl alcohol

triphenylphosphine

→

title compound

المردود 16.2%

5-(5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1-(furan-2-ylmethyl)-1H-tetrazole

المردود 16.2%

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONwas dissolved in tetrahydronfuran (3 ml)
2. 2
   أخرىat 0° C
3. 3
   أخرىthe resulting solution was quenched with saturated ammonium chloride solution (1 ml)
4. 4
   استخلاصThe mixture was extracted with ethyl acetate
5. 5
   أخرىthe solvent of the organic layer was removed under a reduced pressure
6. 6
   أخرىwere separated by silica gel column chromatography (hexane/ethyl acetate=1/5)
7. 7
   أخرىrepurified by reverse phase preparative HPLC
8. 8
   أخرىto obtain two compound, one of which

الإجراء التجريبي

A mixture of 5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1H-tetrazole (113 mg, 0.28 mmol) obtained in Step 1 of Example 52, furfuryl alcohol (0.05 ml, 0.56 mmol) and triphenylphosphine (146 mg, 0.56 mmol) was dissolved in tetrahydronfuran (3 ml) and cooled down to 0° C. Then, diisopropyl azodicarboxylate (0.11 ml, 0.56 mmol) was slowly added thereto at 0° C. After stirring for 2 hours at room temperature, the resulting solution was quenched with saturated ammonium chloride solution (1 ml). The mixture was extracted with ethyl acetate, and then the solvent of the organic layer was removed under a reduced pressure. The residue contained two regioisomers were separated by silica gel column chromatography (hexane/ethyl acetate=1/5), and repurified by reverse phase preparative HPLC, to obtain two compound, one of which was the title compound (22 mg, 16%).

المصدر