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

HRID 1894678Notes

Reaction equation

HRID 1894678 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 AcetateSolvent

Procedure

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

Workup

  1. stirringwas stirred at room temperature
  2. customwhich was separated
  3. washThe ethyl acetate layer was washed with water twice
  4. extractionextracted with ethyl acetate
  5. customThe ethyl acetate layer thus obtained
  6. washwas washed with water twice
  7. customThe previously obtained ethyl acetate layer and the ethyl acetate layer obtained this time
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThis filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-a198ef302da342128572707f1e38f62a
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

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