Methyl 3-(2-methoxyphenyl)propanoate → 5-[4-Methoxy-3-(2-methoxycarbonylethyl)-phenyl]-5-oxo-pentanoic acid methyl ester

HRID 1707292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1707292
[Cl-].[CH3:2][O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][C:8](O)=[O:9].[CH3:12][O:13][C:14](=[O:25])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[CH3:2][O:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][C:8]([C:21]1[CH:20]=[CH:19][C:18]([O:23][CH3:24])=[C:17]([CH2:16][CH2:15][C:14]([O:13][CH3:12])=[O:25])[CH:22]=1)=[O:9]

Komponenten

5

Edukt 3

HCID 562482Methyl 3-(2-methoxyphenyl)propanoateHCID 6451240Aluminum(III) ChlorideHCID 53445129Glutaric acid monomethylester chloride

Produkt 1

HCID 195980155-[4-Methoxy-3-(2-methoxycarbonylethyl)-phenyl]-5-oxo-pentanoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5.1g of glutaric acid monomethyl ester chloride and 5g of 3-(2-methoxyphenyl)-propionic acid methyl ester are added with ice cooling in succession to a suspension of 10g of aluminum chloride in 100 ml of dichloromethane and the mixture is stirred for 16 hours at room temperature. The reaction mixture is poured on ice/2n hydrochloric acid, shaken out with dichloromethane, the organic phase is dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/ethyl acetate (0-30% ethyl acetate). 4.45g of 5-[4-methoxy-3-(2-methoxycarbonylethyl)-phenyl]-5-oxo-pentanoic acid methyl ester is obtained as oil, that is heated together with 47.5g of pyridinehydrochloride for 5 hours to 180° C. for further reaction. After cooling to 90° C. the reaction mixture is mixed with water, acidified to pH 1 with concentrated hydrochloric acid, shaken out with ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. 3.9g of 5[3-(2-carboxyethyl)-4-hydroxyphenyl]-5-oxopentanoic acid of melting point of 169°-166° C. is obtained.

Aufarbeitung

  1. customthe organic phase is dried on sodium sulfate
  2. concentrationconcentrated by evaporation
  3. customThe residue is chromatographed on silica gel with hexane/ethyl acetate (0-30% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-828c27ce269e4932811e05f90f43d320
Quelldatensatz
uspto-grants-1994_10
Patentnummer
US05352701

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