Water → HCID 86644151, compound

HRID 534022Notes

Reaction equation

HRID 534022 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:11]#[C:12][Si](C)(C)C)=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].O.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:4][C:5]1[C:6]([C:11]#[CH:12])=[N:7][CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 2724141Tetrabutylammonium FluorideHCID 67486279HCID 67486279, compound

Product 1

HCID 86644151HCID 86644151, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-((trimethylsilyl)ethynyl)pyridin-3-yl acetate (9.5 g, 41 mmol) in THF (200 mL) was added water (25 ml). The reaction was cooled to 0° C. and TBAF (1M, 45 ml, 45 mmol) was added. The mixture warmed to ambient temperature and stirred for 1 hour. Water (100 mL) was added and the volume was reduced by half. The product was extracted into ether (3×100 mL), washed with brine and dried over MgSO4. The solution was concentrated in vacuo to afford 2-ethynylpyridin-3-yl acetate (5.5 g, 34 mmol) as a light brown oil.

Workup

  1. temperatureThe mixture warmed to ambient temperature
  2. extractionThe product was extracted into ether (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-3c986d73df1149bf9528bd084da3fd57
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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