Tetrahydrofuran → 2-Fluoro-4-(hydroxy(1-methyl-1h-imidazol-5-yl)methyl)benzonitrile

HRID 1594873Notes

Reaction equation

HRID 1594873 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:34]C(=O)C)[C:10]2[N:11]=[CH:12][N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:14]=2)=[CH:5][C:4]=1[F:38])#[N:2].[OH-].[Na+].[CH2:41]1COCC1>O>[F:38][C:4]1[CH:5]=[C:6]([CH:9]([OH:34])[C:10]2[N:11]([CH3:41])[CH:12]=[N:13][CH:14]=2)[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11016583Acetic acid (4-cyano-3-fluoro-phenyl)-(1-trityl-1h-imidazol-4-yl)-methyl ester

Product 1

HCID 185332012-Fluoro-4-(hydroxy(1-methyl-1h-imidazol-5-yl)methyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic acid (4-cyano-3-fluoro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methyl ester (as described in Step C above) (1.26 g, 4.59 mmol) and NaOH (5.5 mL, 5.5 mmol) were dissolved in THF (15 mL) and H2O (25 mL). After 1 h, the reaction was diluted with satd. NaHCO3 solution, extracted with CH2Cl2 (3×), dried (MgSO4) and concentrated to give the title compound.

Workup

  1. additionthe reaction was diluted with satd
  2. extractionNaHCO3 solution, extracted with CH2Cl2 (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25084e115e88460a9d15ac8d1d376df7
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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