Reacción #1153158

Ecuación de reacción

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

hydrogen

→

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

Disolventes

THF ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe catalyst was removed by filtration through Celite®
2. 2
   Lavadothe cake washed with ethanol
3. 3
   Concentraciónthe filtrate concentrated
4. 4
   workup.DISSOLUTIONThe product was dissolved in ether
5. 5
   Filtraciónfiltered through magnesium sulfate
6. 6
   Concentraciónconcentrated
7. 7
   ConcentraciónDuring concentration the product
8. 8
   Otroto crystallize, as the product
9. 9
   Otrocrystallized the mixture
10. 10
    Otrowas flushed with hexanes
11. 11
    Otroto remove the ether
12. 12
    Filtraciónfiltered
13. 13
    Lavadothe cake washed with hexanes
14. 14
    OtroThe yield
15. 15
    Otroupon drying

Procedimiento

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%.

Fuente