Ethyl levulinate → 5-(4-Fluoro-phenyl)-4-methyl-pent-4-enoic acid ethyl ester

HRID 2100471

Reaktionsgleichung

Reaktionsgleichung von HRID 2100471
C([O-])C.[Na+].[Cl-].[F:6][C:7]1[CH:32]=[CH:31][C:10]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:9][CH:8]=1.[C:33]([O:40][CH2:41][CH3:42])(=[O:39])[CH2:34][CH2:35][C:36]([CH3:38])=O.C(OCC)(=O)C.CCCCCC>C(O)C>[CH2:41]([O:40][C:33](=[O:39])[CH2:34][CH2:35][C:36]([CH3:38])=[CH:11][C:10]1[CH:9]=[CH:8][C:7]([F:6])=[CH:32][CH:31]=1)[CH3:42]

Komponenten

6

Edukt 4

HCID 10883Ethyl levulinateHCID 2723922Sodium ethoxideHCID 2733554(4-Fluorobenzyl)triphenylphosphonium chlorideHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 685649295-(4-Fluoro-phenyl)-4-methyl-pent-4-enoic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium ethanolate (0.836 g, 12 mmol) was added under cooling (0° C.) to a solution of 4-fluorobenzyl triphenylphosphonium chloride ([3462-95-1], 5.00 g, 12 mmol) in ethanol, and the mixture was stirred for 45min at r.t. Ethyl levulinate ([539-88-8], 1.77 g, 12 mmol) was added, and the light-orange mixture was refluxed (36 h). After the usual workup, 5-(4-fluoro-phenyl)-4-methyl-pent-4-enoic acid ethyl ester was obtained by column chromatography (silica gel, ethyl acetate/hexane) from the reaction mixture. MS: m/e=237.1 [M+H+].

Aufarbeitung

  1. temperaturethe light-orange mixture was refluxed (36 h)

Quellen und Nachweise

ORD-Eintrag
ord-04ec0a61b131458b8df73ae81e59878f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572801B2

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