Reaktion #50635

ord-0fed15fd2091475685652c7edc9bf58e

Reaktionsgleichung

COc1cc2ccc(=O)oc2cc1O
scopoletine
ClCC1CO1
epichlorohydrin
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[I-].[K+]
potassium iodide
→
COc1cc2ccc(=O)oc2cc1OCC1CO1
(±)-6-methoxy-7-(oxiranylmethoxy)-2H-1-benzopyran-2-one

Edukte

COc1cc2ccc(=O)oc2cc1O
scopoletine
ClCC1CO1
epichlorohydrin
O=C([O-])[O-].[K+].[K+]
potassium carbonate
[I-].[K+]
potassium iodide

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeAfter vacuum evaporation
  2. 2
    Extraktionextraction
  3. 3
    Sonstigewith hot ethanol re-evaporation
  4. 4
    Sonstigefusion point 143°-145° C. (from ethanol)

Vorschrift

25.0 g (130 mmol) of scopoletine, 15.3 ml (196 mmol) epichlorohydrin, 36.0 g (260 mmol) potassium carbonate and 2.5 g of potassium iodide are agitated in 500 ml DMF under nitrogen for 3 h at 80° C. After vacuum evaporation and repeated extraction with hot ethanol re-evaporation was performed. 21.2 g (66%); fusion point 143°-145° C. (from ethanol).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05428038uspto-grants-1995_06