Methyl iodide → 2-Methyl-1-phenyl-2-(pyridin-2-yl)propan-1-one

HRID 907488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907488
[C:1]1([C:7](=[O:16])[CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:19]I>C1COCC1>[CH3:9][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([CH3:19])[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:16]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 115502561-Phenyl-2-(pyridin-2-yl)propan-1-one

Produkt 1

HCID 594074642-Methyl-1-phenyl-2-(pyridin-2-yl)propan-1-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of compound 3 (3.0 g, 14.2 mmol) in THF (10 mL) is added to a suspension of sodium hydride (60%, 0.63 g, 15.6 mmol) in THF (60 mL) at 0° C. The reaction mixture is kept at the same temperature for 2 hours and methyl iodide (0.93 mL, 14.9 mmol) is added at 0° C. The reaction mixture is allowed to warm up to room temperature overnight and then quenched with water. The mixture is separated and the aqueous phase is extracted with ethyl acetate (2×40 mL). The extracts are combined, washed with brine, dried, concentrated and purified by column chromatography (hexane/ethyl acetate 50:1 to 4:1) to give 4 (2.2 g, 69%) as a yellow solid.

Aufarbeitung

  1. customquenched with water
  2. customThe mixture is separated
  3. extractionthe aqueous phase is extracted with ethyl acetate (2×40 mL)
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography (hexane/ethyl acetate 50:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-c71c060800224aa382daa9082c08adf6
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08013165B2

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