Reaktionsgleichung
[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][C:3]=1[O:4][C:5]1[O:9][C:8]([C:10]([O:12]C)=[O:11])=[CH:7][CH:6]=1.[OH-].[Na+]>CO.O>[CH3:1][C:2]1[CH:17]=[CH:16][C:15]([Si:18]([CH3:19])([CH3:21])[CH3:20])=[CH:14][C:3]=1[O:4][C:5]1[O:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of methyl 5-[2-methyl-5-(trimethylsilyl)phenoxy]furan-2-carboxylate (Intermediate 4; 217 mg, 0.71 mmol) in methyl alcohol (3 mL) at room temperature was added a solution of sodium hydroxide (126 mg) in water (1 mL) and the reaction stirred for 18 hours. The resulting mixture was concentrated under reduced pressure, the residue taken up in water and extracted into diethyl ether (1×20 mL). The aqueous layer was acidified with hydrochloric acid (1 M) and extracted with ethyl acetate (2×25 mL). The organic extracts were dried (magnesium sulphate) and concentrated under reduced pressure to give the title compound as a colourless powder (181 mg, 87%). Rf=0.21 (9:1, dichloromethane-methyl alcohol). LCMS Rt=4.33 minutes, m/z=291 (MH+).
Aufarbeitung
- concentrationThe resulting mixture was concentrated under reduced pressure
- extractionextracted into diethyl ether (1×20 mL)
- extractionextracted with ethyl acetate (2×25 mL)
- dry with materialThe organic extracts were dried (magnesium sulphate)
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-7207bda33a6d4baaae05f653b539a24a
- Quelldatensatz
- uspto-grants-2008_08
- Patentnummer
- US07407649B2
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