Lithium Hydroxide → HCID 66654755, compound

HRID 517709Notes

Reaction equation

HRID 517709 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])[CH:12]=2)[N:9]=[N:8][N:7]=1)(=O)C.[Li+].[OH-]>CCO.O>[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])[CH:12]=2)[N:9]=[N:8][N:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68074335{1-[4-cyano-3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate

Product 1

HCID 66654755HCID 66654755, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-[4-cyano-3-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 22, 45 g) in EtOH and water (2:1) was added LiOH (8.21 g, 0.342 mol) at 0° C. The reaction was stirred for 3 hours at room temperature. The solvent was removed under vacuum and the residue diluted with DCM, washed with ice-water, saturated aqueous NaHCO3 and brine. The solution was dried over anhydrous Na2SO4 and the solvent removed under vacuum. The crude product was purified by triturating with ether (500 mL) to yield 4-[5-(hydroxymethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile as a viscous oil (30 g).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue diluted with DCM
  3. washwashed with ice-water, saturated aqueous NaHCO3 and brine
  4. dry with materialThe solution was dried over anhydrous Na2SO4
  5. customthe solvent removed under vacuum
  6. customThe crude product was purified
  7. customby triturating with ether (500 mL)

Sources & evidence

ORD record
ord-143ecc3896a94ab6aa3f10cbf6d8882f
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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