Water → HCID 14249697, compound

HRID 1747527Notes

Reaction equation

HRID 1747527 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:9]([Li])[CH2:10][CH2:11][CH3:12].[Cl-].[NH4+].O>C1COCC1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:1]([OH:8])[CH2:9][CH2:10][CH2:11][CH3:12])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 103713-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 14249697HCID 14249697, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Nicotinaldehyde (0.500 mL, 4.83 mmol) was dissolved in THF (7.0 mL). n-Butyllithium (2.76 mol/L solution in n-hexane, 2.63 mL, 7.25 mmol) was added at −78° C. and the mixture was stirred at the same temperature for 10 minutes. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. 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 Compound A18 (597 mg, 75% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
  7. customto give Compound A18 (597 mg, 75% yield)

Sources & evidence

ORD record
ord-1c62ba9e5fd84c38a749f064c806e219
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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