Water → 3-(2-Pyrimidinyloxy)-benzaldehyde dimethyl acetal

HRID 1275834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275834
[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.CC(C)([O-])C.[K+].Cl[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1.O>CN(C)C=O>[CH3:1][O:2][CH:3]([O:11][CH3:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[CH:5]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 744042-ChloropyrimidineHCID 11275229Phenol, 3-(dimethoxymethyl)-HCID 23665647Potassium tert-butoxide

Produkt 1

HCID 221178593-(2-Pyrimidinyloxy)-benzaldehyde dimethyl acetal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 168 mg of 3-hydroxybenzaldehyde dimethyl acetal in 2 ml of anhydrous dimethylformamide was stirred under nitrogen and 220 mg of potassium tert.butoxide were added. The mixture was heated at 60° C. for 1 hour, then cooled to room temperature and 114 mg of 2-chloropyrimidine were added in portions. The mixture was heated at 150° C. for 20 hours. After cooling 20 ml of water were added and the product was extracted with ethyl acetate. The extracts were washed with 10 ml of 1M sodium hydroxide solution and 5 ml of brine and then dried over anhydrous magnesium sulphate. After filtration and evaporation of the filtrate the residual brown gum was purified by column chromatography on silica gel using ethyl acetate/hexane (1:1) for the elution to give 3-(2-pyrimidinyloxy)-benzaldehyde dimethyl acetal as a syrup.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. temperatureThe mixture was heated at 150° C. for 20 hours
  3. additionwere added
  4. extractionthe product was extracted with ethyl acetate
  5. washThe extracts were washed with 10 ml of 1M sodium hydroxide solution and 5 ml of brine
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationAfter filtration and evaporation of the filtrate the residual brown gum
  8. customwas purified by column chromatography on silica gel
  9. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-c7881455954043e4b313c398881f8d46
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162918

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