Cesium carbonate → 3-Methoxy-2-methoxymethoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde

HRID 1907376

Reaktionsgleichung

Reaktionsgleichung von HRID 1907376
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:56]1[CH:57]=[C:58]([O:68][CH3:69])[C:59]([O:64][CH2:65][O:66][CH3:67])=[C:60]([CH:63]=1)[CH:61]=[O:62]>C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd].[Pd].C(OCC)(=O)C.O1CCOCC1>[CH3:69][O:68][C:58]1[C:59]([O:64][CH2:65][O:66][CH3:67])=[C:60]([CH:63]=[C:56]([N:3]2[CH2:4][CH2:5][O:1][C:2]2=[O:6])[CH:57]=1)[CH:61]=[O:62]

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 739492-OxazolidinoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 115653225-Bromo-3-methoxy-2-(methoxymethoxy)benzaldehyde

Produkt 1

HCID 574825533-Methoxy-2-methoxymethoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehydeAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9832798Tris(dibenzylideneacetone) dipalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-oxazolidinone (0.38 g, 4.36 mmol), dipalladium tris(dibenzylideneacetone) (0.17 g, 0.18 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (XANTPHOS) (0.32 g, 0.55 mmol) and cesium carbonate (1.66 g, 5.1 mmol) were added to a dioxane solution (20 ml) of 5-bromo-3-methoxy-2-methoxymethoxybenzaldehyde (1.0 g, 3.6 mmol) and the mixture was stirred at 100° C. for 24 hours under an argon atmosphere. The reaction solution was cooled to room temperature and ethyl acetate was added thereto. The mixture was filtrated by cerite. The filtrate was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1). The purified product was concentrated under reduced pressure. Ethyl acetate and diisopropyl ether were added to the residue. The insoluble matter thus purified was obtained by filtration and dried to obtain 3-methoxy-2-methoxymethoxy-5-(2-oxo-oxazolidin-3-yl)benzaldehyde (0.5 g) as white powder.

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationThe mixture was filtrated by cerite
  3. washThe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1→1:1)
  7. concentrationThe purified product was concentrated under reduced pressure
  8. additionEthyl acetate and diisopropyl ether were added to the residue
  9. customThe insoluble matter thus purified
  10. customwas obtained by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-86e5a39da223438597cc43ed121aafe4
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598162B2

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