Tetrabutylammonium Fluoride → 2-Ethynyl-5-methylpyridine

HRID 2175419Notes

Reaction equation

HRID 2175419 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][Si](C)(C)C)=[N:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:8]([C:5]1[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1)#[CH:9]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 447549315-Methyl-2-(2-(trimethylsilyl)ethynyl)pyridine

Product 1

HCID 134006342-Ethynyl-5-methylpyridineYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 5-methyl-2-((trimethylsilyl)ethynyl)pyridine (12-1) (4.16 g, 22 mmol) in THF was added tetra-n-butylammonium fluoride (44 mL, 44 mmol) at rt and the solution was stirred for 1 h. The solvent was removed under reduced pressure. The residue was purified by silca gel chromatography with eluent of PE/EA (20/1). The product was obtained as yellow oil (1.78 g, 69%). 1H NMR (400 MHz, CDCl3) δ 8.42 (s, 1H), 7.46 (d, J=7.9 Hz, 1H), 7.38 (d, J=7.9 Hz, 1H), 3.10 (s, 1H), 2.35 (s, 3H); LRMS (ES) calculated M+H for C8H8N, 118.2. Found: 118.3.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by silca gel chromatography with eluent of PE/EA (20/1)

Sources & evidence

ORD record
ord-5c1fac655d404eab8579354b9178782e
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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