Sodium hydride → 3-(2-Methylsulfanylpyrimidin-4-yl)-4-oxo-4-(3-trifluoromethylphenyl)butyric Acid Methyl Ester

HRID 394472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394472
[H-].[Na+].[CH3:3][S:4][C:5]1[N:10]=[C:9]([CH2:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[O:13])[CH:8]=[CH:7][N:6]=1.Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)(O)[O-].[Na+]>CS(C)=O.O>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH:11]([C:9]1[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH3:3])[N:10]=1)[C:12](=[O:13])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:15]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 107574582-[2-(Methylthio)pyrimidin-4-yl]-1-[3-(trifluoromethyl)phenyl]ethanone

Produkt 1

HCID 590837093-(2-Methylsulfanylpyrimidin-4-yl)-4-oxo-4-(3-trifluoromethylphenyl)butyric Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel3×HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (95%, 1.78 g, 83 mmol) and dimethyl sulfoxide (DMSO) (150 mL) were combined under argon in a 3-neck 1L round bottom flask. A solution of Compound 3 in DMSO (50 mL) was added dropwise over 0.75 h using an addition funnel. After stirring an additional 0.5 h, methyl bromoacetate (7.9 mL, 83 mmol) in DMSO (50 mL) was added dropwise. After 18 h, the contents of the reaction flask were poured into water. Saturated sodium bicarbonate was added and the resulting solution was extracted several times with ethyl acetate. The combined organic extracts were washed successively with water and brine. The organic layer was dried with anhydrous sodium sulfate then concentrated in vacuo to give an oil. Purification by flash column chromatography (hexane:ethyl acetate 70:30) afforded Compound 4 as an oil: 24.6 g (64 mmol, 100%)

Aufarbeitung

  1. waitAfter 18 h
  2. extractionthe resulting solution was extracted several times with ethyl acetate
  3. washThe combined organic extracts were washed successively with water and brine
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationthen concentrated in vacuo
  6. customto give an oil
  7. customPurification by flash column chromatography (hexane:ethyl acetate 70:30)

Quellen und Nachweise

ORD-Eintrag
ord-6b2c774bdbf84b1bb0ce2afd5bec093a
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602872B1

Notizen zur Reaktion

Wird geladen…