반응 #1153158

반응 방정식

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

hydrogen

→

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

용매

THF ethanol

반응 조건

후처리

1. 1
   기타The catalyst was removed by filtration through Celite®
2. 2
   세척the cake washed with ethanol
3. 3
   농축the filtrate concentrated
4. 4
   workup.DISSOLUTIONThe product was dissolved in ether
5. 5
   여과filtered through magnesium sulfate
6. 6
   농축concentrated
7. 7
   농축During concentration the product
8. 8
   기타to crystallize, as the product
9. 9
   기타crystallized the mixture
10. 10
    기타was flushed with hexanes
11. 11
    기타to remove the ether
12. 12
    여과filtered
13. 13
    세척the cake washed with hexanes
14. 14
    기타The yield
15. 15
    기타upon drying

실험 절차

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%.

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