Diethyl Ether → HCID 54517921, compound

HRID 2081296Notes

Reaction equation

HRID 2081296 reaction equation
[OH:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[C:4]#[N:5].[C:20](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.CCOCC>CN(C)C=O>[CH3:20][O:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=1)[C:4]#[N:5]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 74004282HCID 74004282, compound

Product 1

HCID 54517921HCID 54517921, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

α-hydroxyimino-2-(4-chlorophenoxy)phenylacetonitrile (a mixture of E- and Z-isomers) (1.36 g, 0.005 mole) was dissolved in dried dimethylformamide (10 ml) and potassium carbonate (0.90 g, 0.0065 mole) was added to the mixture. Further, dimethylsulfate (0.76 g, 0.006 mole) was added to the mixture under ice cooling, followed by stirring at room temperature for 1 hour. Then, ether (150 ml) was added to the mixture, which was washed twice with water. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and then the resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain α-methoxyimino-2-(4-chlorophenoxy)phenylacetonitrile (1.35 g, yield: 94.4%) as a pale yellow oil.

Workup

  1. washwas washed twice with water
  2. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-e1b347ea0e27404c8ec14bf7dd493a7d
Source dataset
uspto-grants-1993_02
Patent number
US05183921

Reaction notes

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