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

HRID 1896674Notes

Reaction equation

HRID 1896674 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. customthe resulting residue was purified by silica gel column chromatography
  3. customto give 120 mg of the title reference compound as a yellow solid

Sources & evidence

ORD record
ord-84e861a890a64bc18100cbe0a01f4f33
Source dataset
uspto-grants-2013_08
Patent number
US08518973B2

Reaction notes

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