Hydrochloric Acid → (4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanol

HRID 62068Notes

Reaction equation

HRID 62068 reaction equation
[F:1][C:2]([F:27])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4].[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO.C(OCC)(=O)C>[F:27][C:2]([F:1])([O:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[N:17][C:16]([C:19]3[CH:26]=[CH:25][C:22]([CH2:23][OH:24])=[CH:21][CH:20]=3)=[N:15]2)=[CH:10][CH:9]=1)[C:3]([F:6])([F:5])[F:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 866333824-[1-(4-pentafluoroethyloxy-phenyl)-1H-[1,2,4]triazol-3-yl]-benzaldehyde

Product 1

HCID 118675138(4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)methanolYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-(1-(4-(perfluoroethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzaldehyde (WO 2011/017513) (3.00 g, 7.83 mmol) in methanol (40 mL) cooled to 0° C. was added sodium borohydride (0.296 g, 7.83 mmol). The reaction mixture was stirred for 1 hour. The mixture was acidified with aqueous hydrogen chloride (1 N) and diluted with ethyl acetate. The pH was adjusted to 7 by aqueous sodium bicarbonate. The organic phase separated, rinsed with saturated aqueous sodium bicarbonate, brine, dried over magnesium sulfate, filtered, and concentrated to provide the title compound as a solid (3.01 g, 100%): ESIMS m/z 386 ([M+H]+).

Workup

  1. customThe organic phase separated
  2. washrinsed with saturated aqueous sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-db7f5624c41440c187695a4f9cdd65f8
Source dataset
uspto-grants-2016_09
Patent number
US09445594B2

Reaction notes

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