Reacción #56617

ord-973bdbdce5b74efa868db36615688a88

Ecuación de reacción

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
Rendimiento 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
Rendimiento 37.3%

Reactantes

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

Reactivos

Ninguno

Disolventes

CC(C)=O
acetone

Condiciones de reacción

Temperatura
-70°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroit was quenched with methanol
  2. 2
    workup.ADDITIONmixed with water
  3. 3
    Extracciónextracted with ethyl acetate
  4. 4
    LavadoThe combined organic phases were washed with a saturated sodium chloride solution
  5. 5
    Otrodried on sodium sulfate
  6. 6
    Concentraciónconcentrated by evaporation in a rotary evaporator

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07419972B2uspto-grants-2008_09