Reaction #56617

ord-973bdbdce5b74efa868db36615688a88

Reaction equation

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
Yield 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
Yield 37.3%

Reactants

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

Reagents

None

Solvents

CC(C)=O
acetone

Conditions

Temperature
-70°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US07419972B2uspto-grants-2008_09