反応 #1153158

反応方程式

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

hydrogen

→

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

溶媒

THF ethanol

反応条件

後処理

1. 1
   その他The catalyst was removed by filtration through Celite®
2. 2
   洗浄the cake washed with ethanol
3. 3
   濃縮the filtrate concentrated
4. 4
   workup.DISSOLUTIONThe product was dissolved in ether
5. 5
   ろ過filtered through magnesium sulfate
6. 6
   濃縮concentrated
7. 7
   濃縮During concentration the product
8. 8
   その他to crystallize, as the product
9. 9
   その他crystallized the mixture
10. 10
    その他was flushed with hexanes
11. 11
    その他to remove the ether
12. 12
    ろ過filtered
13. 13
    洗浄the cake washed with hexanes
14. 14
    その他The yield
15. 15
    その他upon drying

実験手順

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%.

出典