Hydrochloric Acid → 5-[2-(2,2,2-Trifluoro-1-hydroxy-ethyl)-phenyl]-pyridine-2-carbonitrile

HRID 1988025Notes

Reaction equation

HRID 1988025 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[CH:29][C:30]([C:33]#[N:34])=[N:31][CH:32]=1)=[O:20].[F:35][C:36]([Si](C)(C)C)([F:38])[F:37].Cl>C1COCC1>[F:35][C:36]([F:38])([F:37])[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:28]=[CH:29][C:30]([C:33]#[N:34])=[N:31][CH:32]=1)[OH:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 866210895-(2-Formylphenyl)picolinonitrile

Product 1

HCID 667435105-[2-(2,2,2-Trifluoro-1-hydroxy-ethyl)-phenyl]-pyridine-2-carbonitrileYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (5.3 μl, 1.0 M solution in tetrahydrofuran) was added to a solution of 5-(2-formyl-phenyl)-pyridine-2-carbonitrile (110 mg, 0.53 mmol) and trifluoromethyltrimethylsilane (120 μl, 0.81 mmol) in 5 ml THF at 0° C. The formed mixture was warmed up to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then treated with 5 ml of 1N HCl and stirred at room temperature overnight. The product was extracted with ethyl acetate (3×50 ml). The organic layer was separated and dried over sodium sulfate. The organic solvent was evaporated to give 140 mg of 5-[2-(2,2,2-trifluoro-1-hydroxy-ethyl)-phenyl]-pyridine-2-carbonitrile, yield 95%.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionThe product was extracted with ethyl acetate (3×50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe organic solvent was evaporated

Sources & evidence

ORD record
ord-a1f492eaecd34fcfb11484d044589e8c
Source dataset
uspto-grants-2009_06
Patent number
US07553840B2

Reaction notes

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