Water → 4-((Pyridin-2-yloxy)methyl)benzaldehyde

HRID 1691388Notes

Reaction equation

HRID 1691388 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.CN(C)[CH:23]=[O:24].O>O1CCCC1.C(OCC)(=O)C>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:6][C:5]1[CH:14]=[CH:15][C:2]([CH:23]=[O:24])=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 247991602-((4-Bromobenzyl)oxy)pyridineHCID 178418339Butyllithium

Product 1

HCID 592551184-((Pyridin-2-yloxy)methyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-bromo-benzyloxy)-pyridine described in Manufacturing Example 230-1-1 (34 g, 128 mmol) in tetrahydrofuran (120 mL) was added dropwise n-butyl lithium (50 mL, 2.6 M hexane solution, 134 mmol) at −78° C. After stirring for 30 minutes, N,N-dimethyl formamide (10 mL, 134 mmol) was added dropwise to this reaction solution at −78° C., which was stirred at room temperature. Water and ethyl acetate were added to the reaction solution, and liquid separation was carried out. The ethyl acetate layer was washed with water (twice) and sodium chloride water (once). The aqueous layers were combined and extracted with ethyl acetate. The obtained ethyl acetate layer was washed with water (twice) and aqueous sodium chloride (once). The previously obtained ethyl acetate layer and the ethyl acetate layer obtained this time were combined, dried over anhydrous magnesium sulfate, and then filtered. This filtrate was concentrated under a reduced pressure to obtain the title compound (26.8 g) as a crude product.

Workup

  1. stirringwhich was stirred at room temperature
  2. washThe ethyl acetate layer was washed with water (twice) and sodium chloride water (once)
  3. extractionextracted with ethyl acetate
  4. washThe obtained ethyl acetate layer was washed with water (twice) and aqueous sodium chloride (once)
  5. customThe previously obtained ethyl acetate layer and the ethyl acetate layer obtained this time
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThis filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-c8ccda61abb942fd89b6ca002e12b3ae
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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