Sodium Methoxide → 7-Methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid
Reaktionsgleichung
Br[C:2]1[C:3]([C:12]([O:14]C)=[O:13])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1.[CH3:16][O-:17].[Na+]>CN(C=O)C.O>[CH3:16][O:17][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[O:10][CH2:9][CH2:8][O:7][C:6]=2[CH:11]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
In a 2 mL microwave vial, methyl 7-bromo-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylate (273 mg, 1 mmol) and CuBr (14.3 mg, 0.1 mmol) were dissolved in dry DMF and was placed in ice bath. Sodium methoxide (540 mg, 10 mmol) was added into the reaction mixture dropwise while stirring at 0° C. The reaction was warmed to room temperature and stirred for 45 minutes. The reaction was then placed in a microwave reactor for 5 minutes at 135° C. The reaction mixture was dissolved in water and washed with ethyl acetate. The water layer was collected and acidified to pH 4 with 1M HCl. The product was extracted using ethyl acetate then dried over sodium sulfate. The solvent was evaporated under vacuum to give the desired intermediate of 7-methoxy-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid which was used directly without further purification. Yield 57%. MS M+H calculated 211.1, found 211.1.
Aufarbeitung
- temperatureThe reaction was warmed to room temperature
- stirringstirred for 45 minutes
- washwashed with ethyl acetate
- customThe water layer was collected
- extractionThe product was extracted
- dry with materialthen dried over sodium sulfate
- customThe solvent was evaporated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-6ccc54038410469b9726d01a6b4dc400
- Quelldatensatz
- uspto-grants-2012_04
- Patentnummer
- US08148544B2
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