p-Toluenesulfonic acid → 17beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

HRID 2397969Notes

Reaction equation

HRID 2397969 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])[CH2:10][CH2:9]3.[CH:24](S)([SH:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH2:25]1[O:23][C:13]2([CH2:14][C@H:15]([CH3:22])[C@@:16]3([CH2:17][OH:18])[C:11]([CH2:10][CH2:9][C@@H:8]4[C@@H:19]3[CH2:20][CH2:21][C@@:3]3([CH3:4])[C@H:5]4[CH2:6][CH2:7][C@@H:2]3[OH:1])=[CH:12]2)[S:26][CH2:24]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 336451,1-EthanedithiolHCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

Product 1

HCID 2279742417beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

17β,19-Dihydroxy-1αmethyl-4-androsten-3-one in acetic acid is treated with ethanedithiol and p-toluenesulfonic acid. After standing about 4 hours at room temperature, the solution is poured onto water and the mixture extracted with methylenechloride. The methylene-chloride extract is washed well with water, sodium hydroxide solution, water, dried over sodium sulfate and evaporated under reduced pressure to leave 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal which is recrystallized once from acetone-hexane.

Workup

  1. additionthe solution is poured onto water
  2. extractionthe mixture extracted with methylenechloride
  3. extractionThe methylene-chloride extract
  4. washis washed well with water, sodium hydroxide solution, water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fe99a476d43c4b758e310197b47d74a9
Source dataset
uspto-grants-1977_05
Patent number
US04022769

Reaction notes

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