Dimethylformamide → Desmethylamino Methoxy (E)-Metominostrobin

HRID 376032Notes

Reaction equation

HRID 376032 reaction equation
[CH3:1][O:2][C:3](=[O:20])/[C:4](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:5]/[OH:6].[CH3:21]N(C)C=O.[OH-].[K+].COS(OC)(=O)=O>CCOCC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:20])/[C:4](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:5]/[O:6][CH3:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 88276687methyl (2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetate

Product 1

HCID 10803045Desmethylamino Methoxy (E)-MetominostrobinYield 80.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To E-α-hydroxyimino-2-phenoxyphenylacetic acid methyl ester (1.09 g, 0.004 mole) were added dried dimethylformamide (6 ml) and potassium hydroxide (0.29 g, 0.0044 mole) and the mixture was stirred at room temperature for 15 minutes. Then, dried toluene (6 ml) was added to the mixture, to this was further added dropwise dimethylsulfate (0.61 g, 0.0044 mole) under ice cooling. After completion of the addition, the mixture was stirred at room temperature for 2 hours. Then, ether (100 ml) was added, followed by washing with water three times. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain E-α-methoxyimino-2-phenoxyphenyl acetic acid methyl ester (1.20 g, yield: 80.6%) as colorless crystals (melting point: 109 °-110° C.).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. washby washing with water three times
  4. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-0cf9b6c1e5164c98ba731d21babd4566
Source dataset
uspto-grants-1996_01
Patent number
US05488159

Reaction notes

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