Reaktion #5985

ord-624b3fc71b5241e7a87be65e3b8537a0

Reaktionsgleichung

COC(=O)c1cc(Cl)cc(C2CC=CCC2)c1O
methyl 3-(3-cyclohexenyl)-5chlorosalicylate
→
COC(=O)c1cc(Cl)cc2c1O[C@@H]1CCCC[C@@H]21
METHYL 2-CHLORO-TRANS-5a,6,7,8,9,9a-HEXAHYDRODIBENZOFURAN-4-CARBOXYLATE

Edukte

COC(=O)c1cc(Cl)cc(C2CC=CCC2)c1O
methyl 3-(3-cyclohexenyl)-5chlorosalicylate

Reagenzien

Keine

Lösungsmittel

O=C(O)C(F)(F)F
trifluoroacetic acid
—
hexanes

Reaktionsbedingungen

Temperatur
70°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe cooled reaction mixture
  2. 2
    Waschenwashed three times with water
  3. 3
    Sonstigedried
  4. 4
    Sonstigeevaporated to dryness
  5. 5
    SonstigeThe residue is purified with flash chromatography
  6. 6
    Sonstigeto give four fractions

Vorschrift

A mixture of 9 g of methyl 3-(3-cyclohexenyl)-5chlorosalicylate and 20 ml trifluoroacetic acid is heated at 70° C. overnight. The cooled reaction mixture is diluted with hexanes, washed three times with water, dried and evaporated to dryness. The residue is purified with flash chromatography using 10% ethyl acetate/hexane to give four fractions

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246942uspto-grants-1993_09