Lithium hydroxide, monohydrate → 5-[5-(Hydroxymethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrile

HRID 517726Notes

Reaction equation

HRID 517726 reaction equation
O.[OH-].[Li+].C([O:7][CH2:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([C:24]#[N:25])[CH:15]=2)[N:12]=[N:11][N:10]=1)(=O)C>C(O)C.O.CCOC(C)=O>[OH:7][CH2:8][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([CH:15]=2)[C:24]#[N:25])[N:12]=[N:11][N:10]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86691873{1-[3-Cyano-4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate2×

Product 1

HCID 866918745-[5-(Hydroxymethyl)-1H-tetrazol-1-yl]-2-(trifluoromethyl)benzonitrileYield 27.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium hydroxide monohydrate (1.35 g, 32.2 mmol) was added to a solution of {1-[3-cyano-4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl acetate (Intermediate 39, 5.0 g, 16.1 mmol) in a mixture of ethanol and water (2:1) at 0° C. The reaction mixture was stirred for 6 h at room temperature. The reaction mixture was diluted with EtOAc and washed with ice-water. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-60% EtOAc/pet.ether to give the title compound (1.2 g).

Workup

  1. washwashed with ice-water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude compound
  5. customThis was purified by column chromatography (100-200 mesh silica gel)
  6. washeluting with 20%-60% EtOAc/pet

Sources & evidence

ORD record
ord-f131b5b1b96944f4b4dfccd5981d02ee
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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