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

HRID 1930752Notes

Reaction equation

HRID 1930752 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 mL) 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 to separate the reaction solution. The ethyl acetate layer was washed with water (twice) and saline (once). This was combined with the aqueous layer 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 titled compound (26.8 g).

Workup

  1. stirringwas stirred at room temperature
  2. customto separate the reaction solution
  3. washThe ethyl acetate layer was washed with water (twice) and saline (once)
  4. extractionextracted with ethyl acetate
  5. customThe ethyl acetate layer thus obtained
  6. washwas washed with water (twice) and saline (once)
  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-31e5acf3c8e84ba39917586fd6c691d9
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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