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

HRID 1357028Notes

Reaction equation

HRID 1357028 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]=[CH:23][CH:22]=[C:21]([CH3:25])[C:18]=1[CH2:19]Br>CN(C)C=O>[CH3:15][O:16][C:17]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[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 103532222-(Bromomethyl)-1-methoxy-3-methylbenzeneHCID 1363363511-(4,6-Dimethyl-2-pyridinyl)ethanone oxime

Product 1

HCID 854489081-(4,6-Dimethyl-2-pyridinyl)ethanone O-[(2-Methoxy-6-methylphenyl)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 10 ml of N,N-dimethylformamide, and the resultant solution was added with 0.12 g (3.00 mmol) of sodium hydride (60%, oiliness) under cooling with ice. The solution was then stirred for 30 min. at a temperature below 0° C. and then added with the whole amount of the crude product of 2-methoxy-6-methylbenzyl bromide prepared previously under cooling with ice. The resultant solution was stirred for an hour at a room temperature to complete a reaction, and the reacted solution was poured into ice water and subjected to an extraction with diethyl ether. The resultant nonaqueous layer was separated, and the separated layer was washed with water and then dried with anhydrous magnesium sulfate. The dried nonaqueous layer was then condensed under reduced pressure to produce a crude product. The crude product was then purified by means of silica gel column chromatography (eluate; hexane:ethyl acetate=7:3 (v/v)) and recrystallized in hexane to obtain the target compound in an amount of 0.30 g.

Workup

  1. temperatureunder cooling with ice
  2. customprepared previously
  3. temperatureunder cooling with ice
  4. customa reaction
  5. extractionsubjected to an extraction with diethyl ether
  6. customThe resultant nonaqueous layer was separated
  7. washthe separated layer was washed with water
  8. dry with materialdried with anhydrous magnesium sulfate
  9. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-d893e10e1c2a49f0be5265c603b80fc7
Source dataset
uspto-grants-2003_07
Patent number
US06589967B1

Reaction notes

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