Ethyl Acetate → Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate

HRID 508589

Reaktionsgleichung

Reaktionsgleichung von HRID 508589
C(=O)([O-])[O-].[K+].[K+].[CH3:7][NH:8][N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29](Cl)=[O:30])[CH3:18].C(OCC)(=O)C>C(#N)C.CCCCCC>[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29]([N:8]([CH3:7])[N:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:30])[CH3:18]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 574373202,6-Diethyl-4-methylphenylacetyl chlorideHCID 73828661Ethyl 2-(methylhydrazono)propanoate

Produkt 1

HCID 76550641Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoateAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

1.5 g of potassium carbonate was added to a solution of 2.0 g of ethyl 2-(methylhydrazono)propanoate in 35 mL of acetonitrile. The mixture was stirred under cooling with ice, to which a solution of 2.6 g of 2,6-diethyl-4-methylphenylacetyl chloride in 10 mL of acetonitrile was added dropwise over about 20 minutes. The resulting mixture was further stirred for 3.5 hours at room temperature, and then concentrated under reduced pressure. To the residue obtained was added 20 mL of ice-water, which was extracted with ethyl acetate (20 mL×3). The extracts were combined, washed with a saturated sodium chloride aqueous solution (20 mL×2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue obtained was subjected to basic alumina column chromatography (ethyl acetate:hexane=1:3 as eluent) to yield 1.9 g of the title compound as white crystals.

Aufarbeitung

  1. additionwas added dropwise over about 20 minutes
  2. stirringThe resulting mixture was further stirred for 3.5 hours at room temperature
  3. concentrationconcentrated under reduced pressure
  4. customTo the residue obtained
  5. extractionwas extracted with ethyl acetate (20 mL×3)
  6. washwashed with a saturated sodium chloride aqueous solution (20 mL×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained

Quellen und Nachweise

ORD-Eintrag
ord-d8754dd88e3f4ae7b1731c73c8e7904b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096533B2

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