反応 #56617

ord-973bdbdce5b74efa868db36615688a88

反応方程式

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
収率 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
収率 37.3%

反応物

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

試薬

なし

溶媒

CC(C)=O
acetone

反応条件

温度
-70°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他it was quenched with methanol
  2. 2
    workup.ADDITIONmixed with water
  3. 3
    抽出extracted with ethyl acetate
  4. 4
    洗浄The combined organic phases were washed with a saturated sodium chloride solution
  5. 5
    その他dried on sodium sulfate
  6. 6
    濃縮concentrated by evaporation in a rotary evaporator

実験手順

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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07419972B2uspto-grants-2008_09