Potassium Carbonate → Ethyl 2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH:7]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][CH2:26][F:27]>CC(N(C)C)=O>[F:27][CH2:26][CH2:25][C:7]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8]1=[O:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 65 °C
Versuchsvorschrift
To a mixture of ethyl 5-methoxy-1-oxoindane-2-carboxylate (crude product from the preceding two reactions, ˜190 mmol), K2CO3 (53.8 g, 389 mmol) and KI (64.7 g, 390 mmol) in anhydrous dimethylacetamide (792 mL) was added 1-bromo-2-fluoroethane (18.4 mL, 247 mmol) and the mixture was stirred and heated at 65° C. After 20 hours, analysis of an aliquot by NMR showed the reaction to be complete. After cooling to room temperature, most of the dimethylacetamide was removed by evaporation at reduced pressure. The residue was partitioned between EtOAc and water and the organic phase was washed with water (4 times) and brine and dried over Na2SO4. Filtration and removal of the solvent under reduced pressure gave crude ethyl 2-(2-fluoroethyl)-5-methoxy-1-oxoindane-2-carboxylate which was used in the next step without purification.
Aufarbeitung
- customthe reaction
- customwas removed by evaporation at reduced pressure
- customThe residue was partitioned between EtOAc and water
- washthe organic phase was washed with water (4 times) and brine
- dry with materialdried over Na2SO4
- filtrationFiltration and removal of the solvent under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-2b2bb60d002a4136a34f1ac72f33e75f
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07151196B2
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