Ethyl Acetate → [6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

HRID 1644721

Reaktionsgleichung

[F:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[C:4]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[CH:3]=1.C(O[C:25](=O)[CH2:26][CH2:27]C=O)C.[C:31]([O:34][CH2:35][CH3:36])(=[O:33])[CH3:32].[O:37]1CCOCC1>CCCCCC.[Au](Br)(Br)Br>[CH2:35]([O:34][C:31](=[O:33])[CH2:32][C:26]1[CH:27]=[C:10]([C:11](=[O:37])[C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:19])=[O:20])=[CH:16][CH:17]=2)[C:4]2[C:5](=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=2)[CH:25]=1)[CH3:36]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of 4-fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde (1.74 g, 5.77 mmol) and gold(III) bromide (0.15 g, 0.35 mmol) in dioxane (8 mL) was added 4-oxo-butyric acid ethyl ester (1.50 g, 11.53 mmol). The reaction mixture was heated at 100° C. under nitrogen for 4 hours. The solvent was removed in vacuo to afford a deep red viscous oil. Flash chromatography (RediSep® Flash column, 230-400 mesh, 25-65% ethyl acetate in hexane) gave [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (0.63 g, 26%). MS (ESI+) cald. for C22H19FO5S [(M+H)+] 414, obsd. 415. It is noted that in some instances, this reaction also produced some amount of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid.

Aufarbeitung

customThe solvent was removed in vacuo
customto afford a deep red viscous oil

Quellen und Nachweise

ORD-Eintrag: ord-68f953d2e0b54005ba68116fba2e903d
Quelldatensatz: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08124629B2

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