Réaction #56617

ord-973bdbdce5b74efa868db36615688a88

Équation de réaction

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
Rendement 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
Rendement 37.3%

Réactifs

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

Réactifs

Aucun

Solvants

CC(C)=O
acetone

Conditions de réaction

Température
-70°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreit was quenched with methanol
  2. 2
    workup.ADDITIONmixed with water
  3. 3
    Extractionextracted with ethyl acetate
  4. 4
    LavageThe combined organic phases were washed with a saturated sodium chloride solution
  5. 5
    Autredried on sodium sulfate
  6. 6
    Concentrationconcentrated by evaporation in a rotary evaporator

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07419972B2uspto-grants-2008_09