Ethylene Glycol → HCID 86749514, compound

HRID 440723Notes

Reaction equation

HRID 440723 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[CH2:22](O)[CH2:23][OH:24]>C1C=CC=CC=1>[CH2:22]1[CH2:23][O:24][CH:10]2[CH:11]([C@:12]3([CH2:14][CH2:15][C@H:16]4[C@@H:7]([CH2:6][CH2:5][CH:4]5[C@:17]4([CH3:20])[CH2:18][CH2:19][C@H:2]([OH:1])[CH2:3]5)[C@@H:8]3[CH2:9]2)[CH3:13])[O:21]1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 11055399481-29-8

Product 1

HCID 86749514HCID 86749514, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 10.0 g of 3β-hydroxyandrostan-17-one (Elisberg E. et al., J. Amer. Chem. Soc., 1952, 74, 2814) and 0.10 g of p-toluensolfonic acid in 50 ml of benzene and 10 ml of ethylene glycol was kept on standing at reflux temperature for 10 hrs (water was removed by azeotropic distillation). The mixture was pured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, evaporated to dryness under reduced pressure and the crude product was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 as eluant to give 9.0 g of 17-ethylenedioxy-androstan-3β-ol as a colourless oil.

Workup

  1. temperatureat reflux temperature for 10 hrs
  2. custom(water was removed by azeotropic distillation)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customthe crude product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-a7c4588c196e420cad770346a4ce8f60
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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