1-(4-Benzyloxy-phenyl)-5-trifluoromethyl-1H-tetrazole → 4-(5-Trifluoromethyl-tetrazol-1-YL)-phenol

HRID 1065976Notes

Reaction equation

HRID 1065976 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]([C:20]([F:23])([F:22])[F:21])=[N:18][N:17]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>[Pd].C1COCC1.C(O)C>[F:23][C:20]([F:21])([F:22])[C:19]1[N:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[N:16]=[N:17][N:18]=1

Participants

5

Reactant 2

HCID 211972511-(4-Benzyloxy-phenyl)-5-trifluoromethyl-1H-tetrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 211972494-(5-Trifluoromethyl-tetrazol-1-YL)-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Conditions

Temperature
0 °C

Procedure

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%.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. washthe cake washed with ethanol
  3. concentrationthe filtrate concentrated
  4. dissolutionThe product was dissolved in ether
  5. filtrationfiltered through magnesium sulfate
  6. concentrationconcentrated
  7. concentrationDuring concentration the product
  8. customto crystallize, as the product
  9. customcrystallized the mixture
  10. customwas flushed with hexanes
  11. customto remove the ether
  12. filtrationfiltered
  13. washthe cake washed with hexanes
  14. customThe yield
  15. customupon drying

Sources & evidence

ORD record
ord-918077d81930495fbefa65e3f6ae2bb6
Source dataset
uspto-grants-2001_06
Patent number
US06241964B1

Reaction notes

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