Dimethylformamide → alpha-(1-imidazolyl)-2-(4-methylbenzyloxy)benzaldehyde O-methyloxime

HRID 128907Notes

Reaction equation

HRID 128907 reaction equation
CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1.[CH3:21][O:22][N:23]=[C:24]([N:32]1[CH:36]=[CH:35][N:34]=[CH:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[OH:31]>CCOCC>[CH3:21][O:22][N:23]=[C:24]([N:32]1[CH:36]=[CH:35][N:34]=[CH:33]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([CH3:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 77224-Methylbenzyl chlorideHCID 11430Potassium CarbonateHCID 1359761652-hydroxy-alpha-(1-imidazolyl)benzaldehyde O-methyloxime

Product 1

HCID 53962524alpha-(1-imidazolyl)-2-(4-methylbenzyloxy)benzaldehyde O-methyloximeYield 57.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

DMF (3 ml), potassium carbonate (0.22 g) and 4-methylbenzyl chloride (0.20 g) were added to 2-hydroxy-α-(1-imidazolyl)benzaldehyde O-methyloxime (0.26 g), and the mixture was stirred at room temperature overnight. After completion of the reaction, ether (100 ml) was added, and the mixture was washed with brine (80 ml) twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crude product was purified by silica gel chromatography and recrystallized from ethyl acetate/n-hexane to give α-(1-imidazolyl)-2-(4-methylbenzyloxy)benzaldehyde O-methyloxime (0.22 g) as colorless crystals. mp. 70.5°-72.0° C.

Workup

  1. additionwas added
  2. washthe mixture was washed with brine (80 ml) twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting crude product was purified by silica gel chromatography
  6. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-9cb4bad166f44bc9a5c5b06268b18f18
Source dataset
uspto-grants-1995_11
Patent number
US05466661

Reaction notes

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