Tetrabutylammonium Fluoride → 2-Chloro-5-ethynylpyridine

HRID 2109144Notes

Reaction equation

HRID 2109144 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][Si](C)(C)C)=[CH:22][N:21]=1>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][N:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 106322252-Chloro-5-trimethylsilanylethynyl-pyridine

Product 1

HCID 106542812-Chloro-5-ethynylpyridineYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1 M solution of TBAF in THF (12 mL) was added to 500 mg (2.38 mmol) of 2-chloro-5-trimethylsilanylethynyl-pyridine and the black solution was stirred overnight. The mixture was concentrated, the resulting residue was stirred in 50 mL of Et2O for 1 h, and the liquid was decanted from the solids. This washing procedure was repeated twice, and the combined washes were concentrated and chromatographed to provide 240 mg of 2-chloro-5-ethynylpyridine as a colorless solid.

Workup

  1. concentrationThe mixture was concentrated
  2. stirringthe resulting residue was stirred in 50 mL of Et2O for 1 h
  3. customthe liquid was decanted from the solids
  4. concentrationthe combined washes were concentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-161954b79b5840188d0c17563c7fd872
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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