Diethyl Ether → Desmethylamino Methoxy (E)-Metominostrobin

HRID 266415Notes

Reaction equation

HRID 266415 reaction equation
[OH:1]/[N:2]=[C:3](\[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)/C(O)=O.CN(C)[CH:22]=[O:23].[OH-].[K+].COS([O:32][CH3:33])(=O)=O.[CH3:34]COCC>C1(C)C=CC=CC=1>[CH3:22][O:23][C:33](=[O:32])/[C:3](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[N:2]/[O:1][CH3:34]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 88386642(2E)-2-hydroxyimino-2-(2-phenoxyphenyl)acetic acid

Product 1

HCID 10803045Desmethylamino Methoxy (E)-MetominostrobinYield 84.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To E-α-hydroxyimino-2-phenoxyphenylacetic acid (1.29 g, 0.005 mole) were added dried dimethylformamide (10 ml) and 85% potassium hydroxide (0.73 g, 0.011 mole) and the mixture was stirred at room temperature for 15 minutes. Dried toluene (10 ml) was added to the mixture, to which was further added dropwise dimethylsulfate (1.39 g, 0.011 mole) under ice cooling. After completion of the addition, the mixture was stirred at room temperature for 1.5 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-phenoxyphenylacetic acid methyl ester (1.20 g, yield: 84.1%) as colorless crystals (melting point: 109°-110° C.).

Workup

  1. additionAfter completion of the addition
  2. stirringthe mixture was stirred at room temperature for 1.5 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-226f04f942c3451a90126d83651f73bd
Source dataset
uspto-grants-1997_07
Patent number
US05650539

Reaction notes

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