Ethylorthoformate → 2-(2,5-dimethylphenoxymethyl)phenyl 1,3,4-oxadiazol-2-yl ketone O-methyloxime

HRID 1004363Notes

Reaction equation

HRID 1004363 reaction equation
[CH:1]([O-])([O-])OCC.[CH3:7][C:8]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][NH2:22])=[O:20]>O>[CH3:25][O:24][N:23]=[C:18]([C:19]1[O:20][CH:1]=[N:22][N:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][O:10][C:9]1[CH:26]=[C:27]([CH3:30])[CH:28]=[CH:29][C:8]=1[CH3:7]

Participants

4

Reactant 2

HCID 53630039EthylorthoformateHCID 865846752-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetohydrazide

Product 1

HCID 542136592-(2,5-dimethylphenoxymethyl)phenyl 1,3,4-oxadiazol-2-yl ketone O-methyloximeYield 19.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl orthoformate (2 ml) was added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetohydrazide (0.49 g, 1.5 mmol), and the mixture was stirred under reflux for 4 hours. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with dichloromethane. The dichloromethane layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate/n-hexane to give 2-(2,5-dimethylphenoxymethyl)phenyl 1,3,4-oxadiazol-2-yl ketone O-methyloxime (0.10 g, 19.8%) as colorless crystals.

Workup

  1. temperatureunder reflux for 4 hours
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-a2978556c7d748dfb526db56a9f9ac1b
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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