18-Crown-6 → 7-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-phenoxy-phthalide

HRID 1729155

Reaktionsgleichung

Reaktionsgleichung von HRID 1729155
Cl[CH:2]1[C:11]2[C:6](=[C:7]([O:12][C:13]3[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=3)[CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[O:3]1.[C:23]1([O-:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH3:22][O:21][C:15]1[CH:16]=[C:17]([O:19][CH3:20])[N:18]=[C:13]([O:12][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[C:4](=[O:5])[O:3][CH:2]3[O:29][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:14]=1

Komponenten

5

Edukt 3

HCID 2855718-Crown-6HCID 199274063-Chloro-7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-phthalideHCID 23670670Potassium phenoxide

Produkt 1

HCID 199274877-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-phenoxy-phthalide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 1.4 g of 3-chloro-7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-phthalide (see Example 85) and 0.63 g of potassium phenolate is heated at reflux temperature in the presence of a spatula tip of 18-crown-6 in 15 ml of acetonitrile. After 19 hours, the reaction mixture is filtered through Celite® and concentrated by evaporation, and the crude product is purified by column chromatography (eluant 25% ethyl acetate/n-hexane) to yield 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-phenoxy-phthalide in the form of white crystals, m.p. 155°-157° C.

Aufarbeitung

  1. temperatureis heated
  2. filtrationthe reaction mixture is filtered through Celite®
  3. concentrationconcentrated by evaporation
  4. customthe crude product is purified by column chromatography (eluant 25% ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0271a6d3e111443db6b1d992f1aeae74
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05332717

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