Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester → Ethyl 3-(methoxyimino)-3-(4-methoxyphenyl)propanoate

HRID 133788

Reaktionsgleichung

Reaktionsgleichung von HRID 133788
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.[CH3:17][O:18][NH2:19].Cl>C(O)C>[CH3:17][O:18][N:19]=[C:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Komponenten

4

Edukt 2

HCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 521874O-Methylhydroxylamine hydrochloride

Produkt 1

HCID 58984518Ethyl 3-(methoxyimino)-3-(4-methoxyphenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of ethyl 3-(4-methoxyphenyl)-3-oxopropanoate (500 mg) and MeONH2.HCl (207 mg) in ethanol (4 mL) was heated at 80° C. for 2 h. Ethanol was removed in vacuo, and saturated sodium bicarbonate was added to the residue. The aqueous solution was extrated with ethyl acetate (x4), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give the title compound as a colorless oil, which was used directly in the Step B. HPLC retention time: 2.02 min (method A). MS (ESI) (M+H)+ 252.14.

Aufarbeitung

  1. customEthanol was removed in vacuo, and saturated sodium bicarbonate
  2. additionwas added to the residue
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5d0270f549334feb8b9e66f55faeee5c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390925B2

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