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

HRID 557264Notes

Reaction equation

HRID 557264 reaction equation
[O:1]1CCC[CH2:2]1.Br[C:7]1[CH:20]=[CH:19][C:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:9][CH:8]=1.C([Li])CCC.CN(C)C=O>C(OCC)(=O)C.O>[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][CH2:11][C:10]1[CH:19]=[CH:20][C:7]([CH:2]=[O:1])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 247991602-((4-Bromobenzyl)oxy)pyridineHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a tetrahydrofuran solution (120 mL) of 2-(4-bromo-benzyloxy)-pyridine described in Preparation Example 1-4-1 (34 g, 128 mmol) was added n-butyl lithium (50 mL, 2.6M hexane solution, 134 mmol) dropwise at −78° C. After stirring for 30 minutes, to this reaction solution was added N,N-dimethylformamide (10 mL, 134 mmol) dropwise at −78° C, which was stirred at room temperature. To the reaction solution were added water and ethyl acetate to carry out liquid separation. 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 resulting ethyl acetate layer was washed with water (twice) and sodium chloride water (once). The ethyl acetate layer obtained earlier and the ethyl acetate layer obtained this time were combined, dried over anhydrous magnesium sulfate and then filtered. The filtrate thereof 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. customliquid separation
  3. washThe ethyl acetate layer was washed with water (twice) and sodium chloride water (once)
  4. extractionextracted with ethyl acetate
  5. washThe resulting ethyl acetate layer was washed with water (twice) and sodium chloride water (once)
  6. customThe ethyl acetate layer obtained earlier
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate thereof was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-f5d65b92c20d42dbb36fc5a6e92bbf96
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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