Tetrabutylammonium Fluoride → 5-ethynylpyridine-2-carboxylic acid

HRID 1526621Notes

Reaction equation

HRID 1526621 reaction equation
C([Si]([C:8]#[C:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([O:18]C)=[O:17])=[N:14][CH:15]=1)(CC)CC)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:9]([C:10]1[CH:11]=[CH:12][C:13]([C:16]([OH:18])=[O:17])=[N:14][CH:15]=1)#[CH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90389297HCID 90389297, compound

Product 1

HCID 5685815-ethynylpyridine-2-carboxylic acidYield 6.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 5-((triethylsilyl)ethynyl)picolinate (1.68 g, 6.05 mmol) in THF (12.11 ml) was added TBAF, 1.0M in THF (6.68 ml, 6.68 mmol, Sigma Aldrich). The reaction was allowed to stir for 6 hours at RT. The reaction was concentrated. The crude product was adsorbed onto a plug of silica gel and chromatographed through silica gel column eluting with a gradient of 10% to 100% EtOAc in hexane followed by 1% AcOH in EtOAc, to afford 5-ethynylpicolinic acid (0.05 g, 0.37 mmol, 6.10% yield).

Workup

  1. concentrationThe reaction was concentrated
  2. customchromatographed through silica gel column
  3. washeluting with a gradient of 10% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-8b218f6c232740ed97ddd5051ae472de
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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