تفاعل #1153158

معادلة التفاعل

1-(4-benzyloxyphenyl)-5-trifluoromethyl-1H-tetrazole

hydrogen

→

4-(5-Trifluoromethyl-tetrazol-1-yl)-phenol

المذيبات

THF ethanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe catalyst was removed by filtration through Celite®
2. 2
   غسيلthe cake washed with ethanol
3. 3
   تركيزthe filtrate concentrated
4. 4
   workup.DISSOLUTIONThe product was dissolved in ether
5. 5
   ترشيحfiltered through magnesium sulfate
6. 6
   تركيزconcentrated
7. 7
   تركيزDuring concentration the product
8. 8
   أخرىto crystallize, as the product
9. 9
   أخرىcrystallized the mixture
10. 10
    أخرىwas flushed with hexanes
11. 11
    أخرىto remove the ether
12. 12
    ترشيحfiltered
13. 13
    غسيلthe cake washed with hexanes
14. 14
    أخرىThe yield
15. 15
    أخرىupon drying

الإجراء التجريبي

A solution of 129 g (0.40 mol) of 1-(4-benzyloxyphenyl)-5-trifluoromethyl-1H-tetrazole in 900 mL 1:2 THF/ethanol was hydrogenated at ambient temperature over 6 g 10% Pd/C at 45 psi hydrogen for 12 h. The catalyst was removed by filtration through Celite®, the cake washed with ethanol, and the filtrate concentrated. The product was dissolved in ether, filtered through magnesium sulfate and concentrated. During concentration the product began to crystallize, as the product crystallized the mixture was flushed with hexanes to remove the ether. The resulting slurry was cooled to 0° C., aged 1 hr, filtered, and the cake washed with hexanes. The yield upon drying was 84.8 g (91.5%) of white crystalline 4-(5-trifluoromethyl-tetrazol-1-yl)-phenol: 1H NMR (CDCl3) δ 5.6 (s, 1H), 7.07 (m, 2H), 7.35 (m, 2H). MS (EI) m/z 230. Anal. Calcd for C8H5F3N4O: C, 41.75; H, 2.19; F, 24.76; N, 24.34. Found: C, 41.76; H, 2.23; F, 24.53; N, 24.42. KF <0.1%.

المصدر