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Dimethylformamide → Desmethylamino Methoxy (E)-Metominostrobin

HRID 376032
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HRID 376032 반응식
[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]
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참가 물질

7

반응물 4

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

생성물 1

HCID 10803045Desmethylamino Methoxy (E)-Metominostrobin수율 80.6%

시약·촉매·용매 2

HCID 1140
Toluene
용매
HCID 3283Diethyl Ether용매

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-0cf9b6c1e5164c98ba731d21babd4566
출처 데이터셋
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05488159

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