Acetic Anhydride → 4,7-Epoxyisobenzofuran-1,3-dione, hexahydro-

HRID 1524652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524652
C(OC(=O)C)(=O)C.[CH2:8]1[C@H:13]2[O:14][C@H:10]([C@H:11]([C:18]([OH:20])=[O:19])[C@@H:12]2[C:15]([OH:17])=O)[CH2:9]1>C1C=CC=CC=1>[CH2:9]1[CH:10]2[O:14][CH:13]([CH:12]3[C:15](=[O:17])[O:20][C:18](=[O:19])[CH:11]32)[CH2:8]1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 168842rel-(1R,2S,3R,4S)-7-Oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid

Produkt 1

HCID 930044,7-Epoxyisobenzofuran-1,3-dione, hexahydro-Ausbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

As shown in scheme 1, we prepared endothal anhydride by adding acetic anhydride (0.5 mL)(4) to a suspension of Endothall (186 mg)(3) in benzene (3 mL) and the mixture was then stirred until the solid had gone into solution (2 hours). The solution was heated under vacuum to remove the benzene and the residue was then heated at 80° C. for 30 min. Petroleum ether (5 mL) was then added and the desired anhydride spontaneously crystallized. The product was removed by filtration washed with a little petroleum ether to give the pure product (85 mg) which was used immediately in the following two preparations.

Aufarbeitung

  1. customhad gone into solution (2 hours)
  2. temperatureThe solution was heated under vacuum
  3. customto remove the benzene
  4. additionPetroleum ether (5 mL) was then added
  5. customthe desired anhydride spontaneously crystallized
  6. customThe product was removed by filtration
  7. washwashed with a little petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-cf2fed83a19349558be4367f9d562b8a
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079917B2

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