Diethyl Malonate → HCID 70983315, Verbindung

HRID 338901

Reaktionsgleichung

Reaktionsgleichung von HRID 338901
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[CH:8]=[CH:7]2.C([O-])([O-])=O.[Cs+].[Cs+].[C:19]([O:27][CH2:28][CH3:29])(=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(OCC)(=O)C>O1CCOCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.O>[CH3:12][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19]([O:27][CH2:28][CH3:29])=[O:26])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Komponenten

8

Edukt 4

HCID 7761Diethyl MalonateHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 47150308-Bromo-2-methylquinoline

Produkt 1

HCID 70983315HCID 70983315, VerbindungAusbeute 82,54 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 8-bromo-2-methylquinoline (2.00 g, 9.01 mmol), Pd(PtBu3)2 (0.23 g, 0.45 mmol), Cs2CO3 (11.74 g, 36.02 mmol) and diethyl malonate (2.73 mL, 18.01 mmol) in dioxane (25 mL) was heated at 118° C. in a sealed tube for 1 hour. After cooling to ambient temperature, ethyl acetate (30 mL) and water (15 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate) to give diethyl 2-(2-methylquinolin-8-yl)malonate (2.24 g, 82.54%) as an oil.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (7:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-860037163f144b3dbd39da5485ccfc21
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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