Reaktion #1153158

Reaktionsgleichung

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

hydrogen

→

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

Lösungsmittel

THF ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst was removed by filtration through Celite®
2. 2
   Waschenthe cake washed with ethanol
3. 3
   Einengenthe filtrate concentrated
4. 4
   workup.DISSOLUTIONThe product was dissolved in ether
5. 5
   Filtrationfiltered through magnesium sulfate
6. 6
   Einengenconcentrated
7. 7
   EinengenDuring concentration the product
8. 8
   Sonstigeto crystallize, as the product
9. 9
   Sonstigecrystallized the mixture
10. 10
    Sonstigewas flushed with hexanes
11. 11
    Sonstigeto remove the ether
12. 12
    Filtrationfiltered
13. 13
    Waschenthe cake washed with hexanes
14. 14
    SonstigeThe yield
15. 15
    Sonstigeupon drying

Vorschrift

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%.

Quelle