Methyl iodide → 2-(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-3-methoxy-acrylic acid ethyl ester

HRID 38348Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38348
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH3:15])=[CH:9][C:8]=1[CH:16]([CH3:18])[CH3:17])[CH3:2].[H-].[Na+].[CH:22]([O:24][CH2:25]C)=O.IC>COCCOC>[CH2:1]([O:3][C:4](=[O:19])[C:5]([O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH3:15])=[CH:9][C:8]=1[CH:16]([CH3:18])[CH3:17])=[CH:22][O:24][CH3:25])[CH3:2]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 59598614(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester

Produkt 1

HCID 670534762-(2-Isopropyl-4-methoxy-5-methyl-phenoxy)-3-methoxy-acrylic acid ethyl esterAusbeute 23,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of (2-isopropyl-4-methoxy-5-methyl-phenoxy)-acetic acid ethyl ester (4.42 g, 16.6 mmol) in anhydrous 1,2-dimethoxy ethane (60 ml) was added sodium hydride (60% in mineral oil, 3.5 g, 87.5 mmol) at room temperature. After 5 minutes of stirring, ethyl formate (40 ml, 495 mmol) was added. The mixture was heated at 85° C. for 7 hours. After cooling to room temperature, iodomethane was added and stirring was continued overnight. Solvent was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of drying agent, the organic solution was concentrated under reduced pressure. The residue was purified with silica gel chromatography (10% to 30% ethyl acetate in hexane) to yield 2-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-3-methoxy-acrylic acid ethyl ester as a pale yellow oil (1.19 g, 23%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. stirringstirring
  3. waitwas continued overnight
  4. concentrationSolvent was concentrated under reduced pressure
  5. customthe residue was partitioned between ethyl acetate and water
  6. washThe organic phase was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customAfter removal
  9. customof drying agent
  10. concentrationthe organic solution was concentrated under reduced pressure
  11. customThe residue was purified with silica gel chromatography (10% to 30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5eddfb474ea64574adfd0ed09d025926
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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