2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one → 2-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol

HRID 455687

Reaktionsgleichung

Reaktionsgleichung von HRID 455687
[CH:1]([Mg]Cl)=[CH2:2].[CH3:5][O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:21]4[CH:22]=[N:23][CH:24]=[N:25][CH:26]=4)=[CH:14][CH:15]=3)[C:10](=[O:27])[C:9]=2[CH:8]=1>C1COCC1>[CH3:5][O:6][C:7]1[CH:20]=[CH:19][C:18]2[O:17][C:16]3[C:11](=[CH:12][C:13]([C:21]4[CH:26]=[N:25][CH:24]=[N:23][CH:22]=4)=[CH:14][CH:15]=3)[C:10]([CH:1]=[CH2:2])([OH:27])[C:9]=2[CH:8]=1

Komponenten

4

Edukt 2

HCID 574756542-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-oneHCID 178461836HCID 178461836, Verbindung

Produkt 1

HCID 574756552-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

A solution of vinylmagnesium chloride (1.6M solution in THF; 0.82 mL, 1.314 mmol) was added dropwise to a solution of 2-methoxy-7-(pyrimidin-5-yl)-9H-xanthen-9-one (200 mg, 0.657 mmol) in THF (10 mL) at −78° C. After 30 min, the reaction mixture was allowed to warm to −10° C. and was then quenched with saturated aqueous ammonium chloride. The reaction was extracted with EtOAc, and the organic phase was dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography to give 2-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol as a pale yellow gum.

Aufarbeitung

  1. customwas then quenched with saturated aqueous ammonium chloride
  2. extractionThe reaction was extracted with EtOAc
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-384740b203e645908800479fe166b8b2
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08497264B2

Verknüpfte Notizen

Wird geladen…