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Water → 5-(4,6-Dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiophene

HRID 51993
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 51993
[CH:1]([C:3]1[C:8]2[C:9]([CH3:12])=[CH:10][S:11][C:7]=2[CH:6]=[CH:5][C:4]=1[OH:13])=[O:2].[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18](S(C)(=O)=O)[N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18]([O:13][C:4]2[CH:5]=[CH:6][C:7]3[S:11][CH:10]=[C:9]([CH3:12])[C:8]=3[C:3]=2[CH:1]=[O:2])[N:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 190772564-Formyl-5-hydroxy-3-methylbenzothiophene

Produkt 1

HCID 190772825-(4,6-Dimethoxypyrimidin-2-yl)oxy-4-formyl-3-methylbenzothiopheneAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture comprising 2.1 g of 4-formyl-5-hydroxy-3-methylbenzothiophene, 2.4 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 1.8 g of potassium carbonate in 30 ml of N,N-dimethylformamide, was heated and stirred at 70° C. for 3 hours. The mixture was returned to room temperature, then poured into water and extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. Then, it was concentrated under reduced pressure, and the oily substance thereby obtained was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1) to obtain 3.1 g (yield: 86%) of the desired compound.

Aufarbeitung

  1. temperaturewas heated
  2. customwas returned to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThen, it was concentrated under reduced pressure
  7. customthe oily substance thereby obtained
  8. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-b85621a70dcc4cf1a64757f4dd2df935
Quelldatensatz
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05616537

Notizen zur Reaktion

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