Sodium hydride → 1-(4,6-Dimethyl-2-pyridinyl)ethanone O-[(2,4-Dimethoxyphenyl)methyl] Oxime

HRID 1357026Notes

Reaction equation

HRID 1357026 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:9](=[N:11][OH:12])[CH3:10])[CH:3]=1.[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH2:19]Cl>CN(C)C=O>[CH3:15][O:16][C:17]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:18]=1[CH2:19][O:12][N:11]=[C:9]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1)[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 185052611-(Chloromethyl)-2,4-dimethoxybenzene2×HCID 1363363511-(4,6-Dimethyl-2-pyridinyl)ethanone oxime

Product 1

HCID 854489091-(4,6-Dimethyl-2-pyridinyl)ethanone O-[(2,4-Dimethoxyphenyl)methyl] Oxime

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

On the other hand, 0.50 g (3.05 mmol) of 1-(4,6-dimethyl-2-pyridinyl)ethanone oxime was dissolved in 5 ml of N,N-dimethylformamide, and the resultant solution was added with 0.12 g (3.00 mmol) of sodium hydride (60%, oiliness) while cooling the solution with ice. The obtained solution was stirred for 30 min. at a temperature below 0° C. and subsequently added with the whole amount of the toluene solution of 2,4-dimethoxybenzyl chloride prepared previously under cooling with ice. The resultant solution was stirred for 1.5 hours while cooling with ice, and the reacted solution was then poured into icewater, and the ice water containing the reacted solution was extracted with diethyl ether. The resultant nonaqueous layer was separated and washed with water and then dried with anhydrous magnesium sulfate. The dried layer was then condensed under reduced pressure to obtain a crude product. Then, said crude product was purified by means of silica gel column chromatography (eluate; hexane:ethyl acetate=7:3 (v/v)) to obtain the target compound in an amount of 0.62 g. nD20.7; 1.5722

Workup

  1. temperaturewhile cooling the solution with ice
  2. customprepared previously
  3. temperatureunder cooling with ice
  4. temperaturewhile cooling with ice
  5. additionthe reacted solution was then poured into icewater
  6. extractionthe ice water containing the reacted solution was extracted with diethyl ether
  7. customThe resultant nonaqueous layer was separated
  8. washwashed with water
  9. dry with materialdried with anhydrous magnesium sulfate
  10. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-8774ef68924e4ff6b6fe7edbecddd6d8
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Reaction notes

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