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.[CH3:22][O:23][C:24](=[O:29])[CH2:25][C:26]#[C:27]C.C(OCC)(=[O:32])C.Cl[CH2:37][CH2:38]Cl>CCCCCC.[Au](Br)(Br)Br>[CH3:22][O:23][C:24](=[O:29])[CH2:25][C:26]1[C:37]([CH3:38])=[C:10]([C:11](=[O:32])[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:27]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a mixture of 4-fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde (example 2-1, 3rd step) (2.02 g, 6.68 mmol) and pent-3-ynoic acid methyl ester (3.03 g, 26.8 mmol) in 1,2-dichloroethane (40 mL), was added gold(III) bromide (0.264 g, 1.18 mmol). The resulting mixture was heated at 80° C. for 2 hours before additional gold(III) bromide (0.125 g, 0.59 mmol) was added. Another portion of gold(III) bromide (0.125 g, 0.59 mmol) was added after 2 more hours. After a total of 6 hours of heating, the reaction mixture was cooled to room temperature, and the solvent was removed to afford a brown oil. Flash chromatography (Aspire FlashReady™, 50 μm, 30% ethyl acetate in hexane) gave [6-fluoro-4-(4-methanesulfonyl-benzoyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (87 mg, 3.1%). HRMS (ESI+) cald. for C22H19FO5S [(M+Na)+] 437.0829, obsd. 437.0827.
Aufarbeitung
- additionwas added
- temperatureAfter a total of 6 hours of heating
- customthe solvent was removed
- customto afford a brown oil
Quellen und Nachweise
- ORD-Eintrag
- ord-c959dbfcb8bc4d81aa034a9c6ecddd3f
- Quelldatensatz
- uspto-grants-2012_02
- Patentnummer
- US08124629B2
Verknüpfte Notizen
Wird geladen…