Hydrochloric Acid → Cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methanone

HRID 2091207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091207
[OH:1][C:2]1[C:3]([C:8](=O)[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:12][C:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH:15]1([C:13]([C:12]2[O:1][C:2]3[C:3](=[N:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[CH3:9])=[O:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 111600272-Bromo-1-cyclohexylethanoneHCID 140889471-(3-Hydroxypyridin-2-yl)ethan-1-one

Produkt 1

HCID 66777549Cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methanoneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1-(3-hydroxypyridin-2-yl)ethanone (4.37 g), 2-bromo-1-cyclohexylethanone (9.82 g) synthesized in Example A51(1) and N,N-dimethylformamide (50 mL) was added potassium carbonate (13.2 g), and the mixture was stirred at room temperature for 2.5 days. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title object compound (4.09 g, 53%) as a brown solid.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6c074e6de8944d27b331aba49216e674
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436043B2

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