Lithium hydroxide, monohydrate → 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-3-methyl-2-(trifluoromethyl)benzonitrile

HRID 517734Notes

Reaction equation

HRID 517734 reaction equation
C([O:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([C:19]([F:22])([F:21])[F:20])[C:12]=2[CH3:23])[N:9]=[N:8][N:7]=1)(=O)C.O.[OH-].[Li+]>O.O1CCCC1>[OH:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[C:13]([C:19]([F:22])([F:21])[F:20])[C:12]=2[CH3:23])[N:9]=[N:8][N:7]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66655012{1-[4-cyano-2-methyl-3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate2×

Product 1

HCID 666543024-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-3-methyl-2-(trifluoromethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {1-[4-cyano-2-methyl-3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 47, 330 mg, 1.02 mmol) in water (2 mL) and tetrahydrofuran (4 mL), cooled in an ice bath, was added lithium hydroxide monohydrate (42.6 mg, 1.02 mmol). The reaction was stirred at room temperature for 1 hour and 30 min. The organic solvent was removed from the reaction under vacuum and the residual mixture diluted with water (30 mL) and extracted with DCM (2*50 ml). The organic extracts were combined, dried (hydrophobic frit) and the solvent removed to yield the titled compound as a white solid.

Workup

  1. customThe organic solvent was removed from the reaction under vacuum
  2. additionthe residual mixture diluted with water (30 mL)
  3. extractionextracted with DCM (2*50 ml)
  4. customdried (hydrophobic frit)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-b64af645d0d4465b978f7ecfecad7d5f
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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