Reaktion #56617

ord-973bdbdce5b74efa868db36615688a88

Reaktionsgleichung

COCc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
2-methoxymethyl-estra-1,3,5(10)-triene-3,17β-diol
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent
→
COCc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
desired product
Ausbeute 37.3%
COCc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
3-Hydroxy-2-methoxymethyl-estra-1,3,5(10)-trien-17-one
Ausbeute 37.3%

Edukte

COCc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12
2-methoxymethyl-estra-1,3,5(10)-triene-3,17β-diol
CC(C)=O.O=S(=O)(O)O.[O]=[Cr](=[O])=[O]
Jones reagent

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

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

Aufarbeitung

  1. 1
    Sonstigeit was quenched with methanol
  2. 2
    workup.ADDITIONmixed with water
  3. 3
    Extraktionextracted with ethyl acetate
  4. 4
    WaschenThe combined organic phases were washed with a saturated sodium chloride solution
  5. 5
    Sonstigedried on sodium sulfate
  6. 6
    Einengenconcentrated by evaporation in a rotary evaporator

Vorschrift

262 mg (828 μmol) of 2-methoxymethyl-estra-1,3,5(10)-triene-3,17β-diol was dissolved in acetone, cooled to −70° C., and mixed in portions with Jones reagent (1.6 mmol). After 45 minutes, it was quenched with methanol, mixed with water and extracted with ethyl acetate. The combined organic phases were washed with a saturated sodium chloride solution, dried on sodium sulfate, and concentrated by evaporation in a rotary evaporator. Flash chromatography (n-hexane/ethyl acetate) yielded 97 mg (37%) of the desired product as colorless crystals.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07419972B2uspto-grants-2008_09