Reaktion #456225

ord-211dbf26d58a421fb68a5a5085536f0b

Reaktionsgleichung

C[C@]12CC[C@@H]3c4ccc(OC5CCCCO5)cc4C=C[C@H]3[C@@H]1CCC2=C(F)F
17-difluoromethylene-3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraene
O=C(O)C(=O)O
oxalic acid
→
C[C@]12CC[C@@H]3c4ccc(O)cc4C=C[C@H]3[C@@H]1CCC2=C(F)F
17-difluoromethylene-estra-1,3,5(10),6-tetraen-3-ol
Ausbeute 69.7%

Edukte

C[C@]12CC[C@@H]3c4ccc(OC5CCCCO5)cc4C=C[C@H]3[C@@H]1CCC2=C(F)F
17-difluoromethylene-3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraene
O=C(O)C(=O)O
oxalic acid

Reagenzien

Keine

Lösungsmittel

CO
methanol
O
water
O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionextracted with dichloromethane
  2. 2
    Waschenwashed with water, sodium bicarbonate solution as well as with saturated sodium chloride solution
  3. 3
    Sonstigedried on sodium sulfate
  4. 4
    Einengenconcentrated by evaporation in a vacuum
  5. 5
    Sonstigechromatographed on silica gel with hexane/ethyl acetate

Vorschrift

A suspension of 1.1 g of 17-difluoromethylene-3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraene in 25 ml of methanol and 2.5 ml of water is refluxed at a bath temperature of 100° C. with 1.1 mg of oxalic acid for 1.5 hours. Then, it is added to water, extracted with dichloromethane, washed with water, sodium bicarbonate solution as well as with saturated sodium chloride solution, dried on sodium sulfate, concentrated by evaporation in a vacuum and chromatographed on silica gel with hexane/ethyl acetate. 0.6 g of 17-difluoromethylene-estra-1,3,5(10),6-tetraen-3-ol is obtained as colorless crystals with a melting point of 132-134° C., [α]D22 =-167.9° (c=0.505% in pyridine).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06136800uspto-grants-2000_10