Ethyl Acetate → Methyl 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoate

HRID 2272562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272562
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1)#[N:2].[C:19](OCC)(=O)C>S(=O)(=O)(O)O.CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14]([O:16][CH3:19])=[O:15])=[CH:5][CH:4]=1)#[N:2]

Komponenten

5

Edukt 2

HCID 8857Ethyl AcetateHCID 3981627HCID 3981627, Verbindung

Produkt 1

HCID 86729724Methyl 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (940 mg, 3.82 mmol) and conc. sulfuric acid (1 drop) in methanol (25 mL) was heated with reflux for 14 hr. The reaction solution was cooled, and ethyl acetate was added thereto. The solution was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give methyl 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoate (557 mg, 2.139 mmol, 56.0%) as a white powder.

Aufarbeitung

  1. temperaturewith reflux for 14 hr
  2. temperatureThe reaction solution was cooled
  3. washThe solution was washed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1649ecf673174e2ea8250734fefab597
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120776B2

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