Tetrabutylammonium Fluoride → 5-Ethynyl-2-methylpyridine

HRID 2109156Notes

Reaction equation

HRID 2109156 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[CH:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 155537632-Methyl-5-((trimethylsilyl)ethynyl)pyridine

Product 1

HCID 6381975-Ethynyl-2-methylpyridineYield 74.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 654 mg (3.45 mmol) of 2-methyl-5-trimethylsilanylethynyl-pyridine and 8 mL of 1 M TBAF in THF was stirred for 2 h. The mixture was concentrated and chromatographed (10-50% EtOAc in hexanes) to provide 301 mg of 2-methyl-5-ethynyl pyridine.

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed (10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ee1974fe7bd04180adecbff229e90192
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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