Reaktionsgleichung
[OH-].[Li+].C[O:4][C:5](=[O:30])[CH2:6][C:7]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:20][CH:19]=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:29])[CH:13]=2)[CH:8]=1.Cl>O1CCCC1>[CH2:27]([S:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([F:29])[CH:13]=3)[CH:8]=[C:7]([CH2:6][C:5]([OH:30])=[O:4])[CH:16]=2)=[CH:19][CH:20]=1)(=[O:25])=[O:26])[CH3:28]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
5 N lithium hydroxide (6 mL) was added to a solution of [4-(4-ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester (64 mg, 0.16 mmol) in tetrahydrofuran (4 mL). After being stirred at room temperature overnight, the resulting mixture was acidified to pH 3 with 5 N hydrochloric acid, and then extracted with ethyl acetate (10 mL×2). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was precipitated from ethyl ester/petroleum ether (1:10) to give [4-(4-ethanesulfonyl-phenoxy)-6-fluoro-naphthalen-2-yl]-acetic acid (25 mg) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.84-7.90 (m, 3H), 7.65 (s, 1H), 7.57 (dd, J=9.85, 2.53 Hz, 1H), 7.33 (td, J=8.65, 2.65 Hz, 1H), 7.09-7.14 (m, 3H), 3.80 (s, 2H), 3.13 (q, J=7.33 Hz, 2H), 1.30 (t, J=7.45 Hz, 3H); MS cald. for C20H17FO5S 388, obsd. (ESI+) [(M+H)+] 389.
Aufarbeitung
- extractionextracted with ethyl acetate (10 mL×2)
- dry with materialThe organic layers were dried over sodium sulfate
- concentrationconcentrated in vacuo
- customThe residue was precipitated from ethyl ester/petroleum ether (1:10)
Quellen und Nachweise
- ORD-Eintrag
- ord-bf7b5313728841b6873a0664036c950b
- Quelldatensatz
- uspto-grants-2014_02
- Patentnummer
- US08642629B2
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