Tetrabutylammonium Fluoride → 4-(2-Hydroxyethyl)pyridine-2-carbonitrile

HRID 586356Notes

Reaction equation

HRID 586356 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][N:14]=[C:13]([C:17]#[N:18])[CH:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.C(OCC)(=O)C>[C:17]([C:13]1[CH:12]=[C:11]([CH2:10][CH2:9][OH:8])[CH:16]=[CH:15][N:14]=1)#[N:18]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 223217094-(Tert-butyl-dimethylsilyloxyethyl)-2-cyanopyridine

Product 1

HCID 223216614-(2-Hydroxyethyl)pyridine-2-carbonitrileYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[2-(tert-Butyldimethylsilyloxy)ethyl]-2-cyanopyridine (12.8 g, 48.8 mmol) and a solution of tetrabutylammonium fluoride (1 M in THF, 73 mL, 73 mmol) were charged to a round bottom flask and stirred at room temperature overnight. The mixture was diluted with water and ethyl acetate. The layers were separated and the water layer extracted with ethyl acetate. The organic layers were combined, washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography (SiO2, 50:1 CH2Cl2: methanol) to provide 2-cyano-4-(2-hydroxyethyl)pyridine (4.4 g, 61%) as an off white solid.

Workup

  1. customThe layers were separated
  2. extractionthe water layer extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (SiO2, 50:1 CH2Cl2: methanol)

Sources & evidence

ORD record
ord-2954b96f3f464ab9a6e91a81d3d5925e
Source dataset
uspto-grants-2005_08
Patent number
US06936611B2

Reaction notes

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