Potassium Carbonate → HCID 86678196, compound

HRID 1747542Notes

Reaction equation

HRID 1747542 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][CH:10]([O:23][CH2:24][CH3:25])[C:11]1[CH:12]=[CH:13][C:14]([C:17]#[C:18][Si](C)(C)C)=[N:15][CH:16]=1)[CH3:8]>CO>[CH2:24]([O:23][CH:10]([O:9][CH2:7][CH3:8])[C:11]1[CH:12]=[CH:13][C:14]([C:17]#[CH:18])=[N:15][CH:16]=1)[CH3:25]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86678195HCID 86678195, compound

Product 1

HCID 86678196HCID 86678196, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In THF (10 mL) was dissolved 2-bromo-5-(diethoxymethyl)pyridine (1.00 g, 3.84 mmol) obtained in Step 1. To the solution were added trimethylsilyl acetylene (1.09 mL, 7.69 mmol), copper iodide (I) (37.0 mg, 0.192 mmol), (bistriphenylphosphine) palladium (II) chloride (135 mg, 0.192 mmol), and triethylamine (1.07 mL, 7.69 mmol), and the mixture was stirred at 70° C. for 6 hours. The solvent in the reaction mixture was evaporated under reduced pressure, and water and ethyl acetate were added. The mixture was filtered through Celite and the filtrate was extracted with ethyl acetate. Washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give 5-(diethoxymethyl)-2-((trimethylsilyl)ethynyl)pyridine (1.07 g). In methanol (10 mL) was dissolved 5-(diethoxymethyl)-2-((trimethylsilyl)ethynyl)pyridine obtained. Potassium carbonate (1.06 g, 7.69 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The solvent in the reaction mixture was evaporated under reduced pressure, and water was added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 5-(diethoxymethyl)-2-ethynylpyridine (703 mg, 89% yield).

Workup

  1. customobtained
  2. customThe solvent in the reaction mixture was evaporated under reduced pressure, and water
  3. additionwas added
  4. extractionExtraction with ethyl acetate
  5. washwashing with saturated brine
  6. dry with materialdrying over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. customthe solvent in the filtrate was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-9c70014a8ea345a58c22af5309f51f31
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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