Reaktion #456223

ord-81ce56f962214315aba1bd3595401140

Reaktionsgleichung

C[C@]12CC[C@@H]3c4ccc(O)cc4C=C[C@H]3[C@@H]1CCC2=O
3-hydroxy-estra-1,3,5(10),6-tetraen-17-one
C1CCOC1
tetrahydrofuran
Cc1ccc(S(=O)(=O)O)cc1
para-toluenesulfonic acid
→
C[C@]12CC[C@@H]3c4ccc(OC5CCCCO5)cc4C=C[C@H]3[C@@H]1CCC2=O
3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraen-17-one

Edukte

C[C@]12CC[C@@H]3c4ccc(O)cc4C=C[C@H]3[C@@H]1CCC2=O
3-hydroxy-estra-1,3,5(10),6-tetraen-17-one
C1CCOC1
tetrahydrofuran
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

Vorschrift

A suspension of 2.6 g of 3-hydroxy-estra-1,3,5(10),6-tetraen-17-one in 26 ml of tetrahydrofuran and 2.6 ml of dihydropyran is stirred with 12.3 mg of para-toluenesulfonic acid for 3 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 and concentrated by evaporation in a vacuum. 3.0 g of 3-tetrahydropyranyloxy-estra-1,3,5(10),6-tetraen-17-one is obtained as colorless crystals.

Quelle

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