Dimethylformamide → Ethyl 2-(4,6-dimethylpyrimidin-2-yl)oxyacetate

HRID 1886300

Reaktionsgleichung

Reaktionsgleichung von HRID 1886300
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:14][OH:15].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:15][CH2:14][C:13]([O:17][CH2:18][CH3:19])=[O:16])[N:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 12184Ethyl GlycolateHCID 27723824,6-Dimethyl-2-methylsulfonylpyrimidine

Produkt 1

HCID 3410252Ethyl 2-(4,6-dimethylpyrimidin-2-yl)oxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution containing 4,6-dimethyl-2-methylsulfonylpyrimidine (10.0 g, 53.8 mmol), ethyl glycolate (5.60 g, 53.8 mmol), and 30 mL of N,N -dimethylformamide was prepared and to this was added with stirring potassium carbonate (8.0 g, 60 mmol). The mixture was allowed to stir at ambient temperature overnight. It was then poured into water and the resulting mixture was extracted 3 times with ethyl acetate. The combined organic extracts were extracted with water. The aqueous extract was saturated with sodium chloride and extracted twice more with ethyl acetate. All of the ethyl acetate layers were combined, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 8.20 g (72.6 percent of theory) of the title compound as a yellow oil. This oil was filtration chromatographed on silica gel, eluting with a 30:70 mixture of ethyl acetate and hexane. The product containing eluate was concentrated by evaporation under reduced pressure to obtain 7.9 g (70 percent of theory) of the title compound as a colorless oil which solidified on standing to a white solid melting at 57°-59° C.

Aufarbeitung

  1. customwas prepared
  2. extractionthe resulting mixture was extracted 3 times with ethyl acetate
  3. extractionThe combined organic extracts were extracted with water
  4. extractionThe aqueous extract
  5. extractionextracted twice more with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d3d9b63ea6e449bc91fb52632da38ab6
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05151113

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