(Trifluoromethyl)trimethylsilane → 2-Pyridinecarbonitrile, 5-(2,2,2-trifluoro-1-hydroxyethyl)-

HRID 1186406Notes

Reaction equation

HRID 1186406 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([CH:9]=[O:10])=[CH:5][CH:4]=1)#[N:2].[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([OH:10])[C:12]([F:14])([F:13])[F:11])=[CH:7][N:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 109862635-Formylpyridine-2-carbonitrile

Product 1

HCID 670859302-Pyridinecarbonitrile, 5-(2,2,2-trifluoro-1-hydroxyethyl)-Yield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 6-cyano-3-pyridinecarboxaldehyde (364 mg, 2.76 mmol), (trifluoromethyl)trimethylsilane (490 μL, 3.31 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 276 μL, 0.276 mmol) and tetrahydrofuran (7.0 mL), the mixture was stirred and reacted at room temperature for 5 hours. Then, purification by column chromatography (hexane/ethyl acetate=7/3) was performed to give 2-cyano-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine (Compound ES) (455 mg, yield: 82%).

Workup

  1. customreacted at room temperature for 5 hours
  2. customThen, purification by column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-ba1eb7f5927b41918a4d166975c7c3c6
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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