Potassium Phosphate, Tribasic → Methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate
Reaktionsgleichung
CB(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:13]1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Cl[C:48]1[C:52]2[CH:53]=[C:54]([O:57][CH3:58])[CH:55]=[CH:56][C:51]=2[S:50][C:49]=1[C:59]([O:61][CH3:62])=[O:60]>O1CCOCC1.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:58][O:57][C:54]1[CH:55]=[CH:56][C:51]2[S:50][C:49]([C:59]([O:61][CH3:62])=[O:60])=[C:48]([CH3:13])[C:52]=2[CH:53]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 4
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Methyl boronic acid (120 mg), potassium phosphate (849 mg), water (0.30 ml), palladium acetate (22 mg), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl (95 mg) were added to a solution of methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylate (257 mg) in 1,4-dioxane (3.0 ml), and the reaction solution was stirred at 100° C. for 12 hours. The reaction solution was diluted with ethyl acetate and washed successively with an aqueous ammonium chloride solution, an aqueous sodium bicarbonate solution, and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate) to obtain methyl 5-methoxy-3-methylbenzo[b]thiophene-2-carboxylate.
Aufarbeitung
- washwashed successively with an aqueous ammonium chloride solution
- dry with materialAfter drying over anhydrous sodium sulfate
- customthe solvent was evaporated under vacuum
- customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane-ethyl acetate)
Quellen und Nachweise
- ORD-Eintrag
- ord-ade2f2939fc04385b686a0b1e7d7f253
- Quelldatensatz
- uspto-grants-2015_09
- Patentnummer
- US09145414B2
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