Epichlorohydrin → 1-hydroxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-one

HRID 83093

Reaktionsgleichung

Reaktionsgleichung von HRID 83093
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([OH:17])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl>CC(C)=O>[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[CH:5]=[C:4]([O:17][CH2:24][CH:26]2[CH2:27][O:28]2)[CH:3]=1

Komponenten

5

Edukt 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 54881931,3-Dihydroxy-xanthone

Produkt 1

HCID 105171431-hydroxy-3-(oxiran-2-ylmethoxy)-9H-xanthen-9-oneAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
57.5 °C

Versuchsvorschrift

1,3-dihydroxy-9H-xanthen-9-one (1 g, 4.39 mmol) prepared in Step 1 of Example 2 and K2CO3 (1.52 g, 10.98 mmol) were added to a dry round-bottom flask, and anhydrous acetone (25 ml) was added thereto. Epichlorohydrin (1.73 mL, 21.95 mmol) was added dropwise to the reaction mixture, and the reaction liquid was stirred under reflux at a temperature of 55 to 60° C. for 6 hours. After the reaction was completed, the solvent was removed under reduced pressure. The resulting residue was separated and purified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v)) to give the title compound (0.28 g, 22%) as a light brown solid.

Aufarbeitung

  1. customthe reaction liquid
  2. customthe solvent was removed under reduced pressure
  3. customThe resulting residue was separated
  4. custompurified by silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-07e7999c8d4f4167b703d2f440767984
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846749B2

Verknüpfte Notizen

Wird geladen…