Ethylene Glycol → HCID 70433074, compound

HRID 652713Notes

Reaction equation

HRID 652713 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH2:14][C@@H:15]1[CH3:21])[CH2:10][CH2:9]3.[CH2:23](O)[CH2:24][OH:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:23]1[CH2:24][O:25][C:13]2([CH2:14][C@H:15]([CH3:21])[C@@:16]3([CH3:17])[C:11](=[CH:10][CH2:9][C@@H:8]4[C@@H:18]3[CH2:19][CH2:20][C@@:3]3([CH3:4])[C@H:5]4[CH2:6][CH2:7][C@@H:2]3[OH:1])[CH2:12]2)[O:22]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 10179417beta-Hydroxy-1alpha-methylandrost-4-ene-3-one

Product 1

HCID 70433074HCID 70433074, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 7.0 g of 17β-hydroxy-1α-methyl-4-androsten-3-one in 500 ml of benzene is combined with 80 ml of 1,2-ethanediol and 400 mg of p-toluenesulfonic acid and the evolving water is distilled off azeotropically within 20 hours. After cooling of the reaction mixture, the latter is combined with 5 ml of pyridine, washed with water, dried over sodium sulfate, and concentrated under vacuum. The residue is chromatographed on silica gel, thus obtaining with hexane-ethyl acetate gradients (25-30% ethyl acetate) 6.3 g of 3,3-ethylenedioxy-1α-methyl-5-androsten-17β-ol.

Workup

  1. distillationthe evolving water is distilled off azeotropically within 20 hours
  2. temperatureAfter cooling of the reaction mixture
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-c0971bade7f2440aa5cac93fb7b318f3
Source dataset
uspto-grants-1987_06
Patent number
US04673673

Reaction notes

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