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Hydrochloric Acid → 3-Vinyl-phthalide

HRID 22164
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 22164
COC1C=C(OC)N=C(O[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=O)[O:18][CH:17]3[OH:22])N=1.[CH:23]([Mg]Cl)=[CH2:24].Cl>O1CCCC1>[CH:23]([CH:19]1[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17](=[O:22])[O:18]1)=[CH2:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 199274177-[(4,6-Dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalideHCID 178461836HCID 178461836, Verbindung2×

Produkt 1

HCID 185154913-Vinyl-phthalide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

3.6 g of 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxyphthalide (see Example 84) are placed in 60 ml of absolute tetrahydrofuran at -45° C., and the solution is treated within 10 minutes with 18 ml of a 2M solution of vinylmagnesium chloride solution in tetrahydrofuran. The reaction solution is then stirred for approximately 16 hours at room temperature, a further 6 ml of vinylmagnesium chloride solution are added and the reaction solution is heated at reflux temperature for a further hour. When it has cooled, the reaction solution is acidified with 1N hydrochloric acid and freed of tetrahydrofuran in a rotary evaporator. The aqueous phase is then extracted with tert-butyl methyl ether, and the organic phase in washed and concentrated by evaporation under reduced pressure. Silica gel chromatography using ethyl acetate/n-hexane (2:3) as eluant yields pure 7-[4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-vinyl-phthalide, m.p. 94°-97° C.

Aufarbeitung

  1. temperaturethe reaction solution is heated
  2. temperatureat reflux temperature for a further hour
  3. temperatureWhen it has cooled
  4. customfreed of tetrahydrofuran in a rotary evaporator
  5. extractionThe aqueous phase is then extracted with tert-butyl methyl ether
  6. washthe organic phase in washed
  7. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2f00ffffabf4475ca736d5316f5ba45b
Quelldatensatz
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05428002

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