Reaktion #938024

ord-27c1ce5ed6e6427f9215d23083d74476

Reaktionsgleichung

C[C@H]1Cc2cc(O)ccc2[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@@H]21
3-hydroxy-7β-methyl-estra -1,3,5(10)-trien-17-one
Cc1ccccc1
toluene
Cc1ccc(S(=O)(=O)O)cc1
para-toluenesulfonic acid
→
C[C@H]1Cc2cc(OC3CCCCO3)ccc2[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@@H]21
7β-methyl-3-tetrahydropyranyloxy-estra-1,3,5(10)-trien-17-one

Edukte

C[C@H]1Cc2cc(O)ccc2[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@@H]21
3-hydroxy-7β-methyl-estra -1,3,5(10)-trien-17-one
Cc1ccccc1
toluene
Cc1ccc(S(=O)(=O)O)cc1
para-toluenesulfonic acid

Reagenzien

Keine

Lösungsmittel

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

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 1.2 g of 3-hydroxy-7β-methyl-estra -1,3,5(10)-trien-17-one in 12 ml of toluene and 1.2 ml of dihydropyran is stirred with 5.6 mg of para-toluenesulfonic acid for 2 hours at room temperature. Then, it is 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. 1.22 g of 7β-methyl-3-tetrahydropyranyloxy-estra-1,3,5(10)-trien-17-one is obtained.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06018062uspto-grants-2000_01