Tetrabutylammonium Fluoride Trihydrate → 4-(Hydroxymethyl)pyridine-2-carbonitrile

HRID 493231Notes

Reaction equation

HRID 493231 reaction equation
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:22]([C:24]1[CH:29]=[C:28]([CH2:30][O:31][Si](C)(C)C)[CH:27]=[CH:26][N:25]=1)#[N:23]>O1CCCC1>[C:22]([C:24]1[CH:29]=[C:28]([CH2:30][OH:31])[CH:27]=[CH:26][N:25]=1)#[N:23]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 230937972-Cyano-4-(trimethylsilyloxymethyl)pyridine

Product 1

HCID 107253914-(Hydroxymethyl)pyridine-2-carbonitrileYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetra-n-butylammonium fluoride trihydrate (1.1 g, 3.5 mmol) was added to a solution of 2-cyano-4-(trimethylsilyloxymethyl)pyridine (600 mg, 2.9 mmol, Reference compound No. 10-1) in tetrahydrofuran (15 mL) at room temperature, then the mixture was stirred for 3 hours. The solvent was evaporated under reduced pressure, and then the resulting residue was purified- by silica gel column chromatography to give 120 mg of the title reference compound as a yellow solid. (Yield 32%)

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto give 120 mg of the title reference compound as a yellow solid

Sources & evidence

ORD record
ord-ea1c0e880a8c4d2894526979b904b444
Source dataset
uspto-grants-2009_05
Patent number
US07534802B2

Reaction notes

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