Methyl 4-fluorobenzoylacetate → HCID 86658322, Verbindung

HRID 1890270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890270
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[Cl-].[CH3:16][CH:17]1[CH2:21][CH2:20][C:19](=[O:22])[N:18]1[NH3+:23]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:23][N:18]2[C:19](=[O:22])[CH2:20][CH2:21][CH:17]2[CH3:16])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 579425Methyl 4-fluorobenzoylacetateHCID 67437276HCID 67437276, Verbindung

Produkt 1

HCID 86658322HCID 86658322, VerbindungAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 7.50 g (38.2 mmol) of methyl 3-(4-fluorophenyl)-3-oxopropanoate and 11.5 g (76.5 mmol) of 2-methyl-5-oxopyrrolidin-1-aminium chloride in 50 ml of pyridine is stirred at room temperature for 72 h. The reaction mixture is concentrated under reduced pressure. Purification by column chromatography on silica gel (cyclohexane/ethyl acetate) gives 10.4 g (93%) of the desired product as a mixture of isomers; log P(HCOOH): 2.13 and 2.45; 1H-NMR (ppm): δ (DMSO-d6)=1.16-1.19 (m, 3H), 1.58-1.62 (m, 2H), 2.20-2.22 (m, 1H), 2.36-2.41 (m, 1H), 3.54 (s, 2.25H), 3.64 (s, 0.75H), 3.80 (d, 1H), 3.90 (d, 1H), 3.80 (q, 1H), 7.24 (t, 0.6H), 7.29 (t, 1.4H), 7.44-7.47 (m, 0.6H), 7.89-7.92 (m, 1.4H); LC-MS: m/z=293 [M+H]+.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customPurification by column chromatography on silica gel (cyclohexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8588c0f702404ffb8dedc474e606fe99
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507472B2

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