Cesium carbonate → 1-(1,3-Dioxolan-2-ylmethyl)-7-methylquinolin-2(1h)-one

HRID 39686

Reaktionsgleichung

Reaktionsgleichung von HRID 39686
Br[CH2:2][CH:3]1[O:7][CH2:6][CH2:5][O:4]1.[CH3:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.CS(C)=O>[O:4]1[CH2:5][CH2:6][O:7][CH:3]1[CH2:2][N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([CH3:8])[CH:18]=2)[CH:13]=[CH:14][C:15]1=[O:19]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 776737-Methyl-2-quinoloneHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 516892Sodium Bicarbonate

Produkt 1

HCID 593978351-(1,3-Dioxolan-2-ylmethyl)-7-methylquinolin-2(1h)-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To 6.3 mL of a dimethyl sulfoxide solution containing 1.1 g of 2-bromomethyl-1,3-dioxolane, 1.0 g of 7-methylquinolin-2(1H)-one and 3.1 g of cesium carbonate were added, and the mixture was stirred at 60 to 70° C. for 1 hour. The reaction mixture was added with ethyl acetate, water and an aqueous saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3] to obtain 0.60 g of a brown oily substance, 1-(1,3-dioxolan-2-ylmethyl)-7-methylquinolin-2(1H)-one.

Aufarbeitung

  1. additionwere added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [eluent; hexane:ethyl acetate=2:3]

Quellen und Nachweise

ORD-Eintrag
ord-9041a22baa42428fbde1e34aa3e447f7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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