Reaktion #456243

ord-dbbd6ce2084c405784513d116580301b

Reaktionsgleichung

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@@H]3[C@@H]1CCC2=O
3-hydroxy-8a-estra-1,3,5(10)-trien-17-one
Cc1ccc(S(=O)(=O)O)cc1
para-toluenesulfonic acid
c1ccncc1
pyridine
→
C[C@]12CC[C@@H]3c4ccc(OC5CCCCO5)cc4CC[C@@H]3[C@@H]1CCC2=O
3-tetrahydropyranyloxy-8a-estra-1,3,5(10)-trien-17-one

Edukte

C[C@]12CC[C@@H]3c4ccc(O)cc4CC[C@@H]3[C@@H]1CCC2=O
3-hydroxy-8a-estra-1,3,5(10)-trien-17-one
Cc1ccc(S(=O)(=O)O)cc1
para-toluenesulfonic acid
c1ccncc1
pyridine

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
ethyl acetate
C1CCOC1
tetrahydrofuran
C1=COCCC1
dihydropyran

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with sodium bicarbonate solution as well as with saturated sodium chloride solution
  2. 2
    Sonstigedried on sodium sulfate
  3. 3
    Einengenconcentrated by evaporation in a vacuum
  4. 4
    Sonstigechromatographed on silica gel with hexane/acetone

Vorschrift

A suspension of 2.0 g of 3-hydroxy-8a-estra-1,3,5(10)-trien-17-one in 20 ml of tetrahydrofuran and 2.0 ml of dihydropyran is stirred with 15 mg of para-toluenesulfonic acid for 24 hours at room temperature. Then, 0.3 ml of pyridine is added, diluted with ethyl acetate, washed with 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/acetone. 2.2 g of 3-tetrahydropyranyloxy-8a-estra-1,3,5(10)-trien-17-one is obtained as colorless crystals with a melting point of 153-155° C., [α]D22 =+47.5° (c=0.53% in pyridine).

Quelle

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