p-Toluenesulfonic acid → HCID 22801518, compound

HRID 1834992Notes

Reaction equation

HRID 1834992 reaction equation
[OH:1][C@@:2]1([CH3:23])[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@H:11]([CH2:12][C:13](=[O:22])[CH2:14][CH2:15]1)[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:22][C:13]2([CH2:14][CH2:15][C@@:16]3([CH2:17][OH:18])[C@@H: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@@:2]3([OH:1])[CH3:23])[CH2:12]2)[S:26][CH2:24]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 336451,1-EthanedithiolHCID 70614615HCID 70614615, compound

Product 1

HCID 22801518HCID 22801518, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

17β,19-Dihydroxy-17α-methyl-5α-androstan-3-one in acetic acid is treated with ethanedithiol and p-toluenesulfonic acid. After standing for 4 hours at room temperature, the solution is poured onto water and the mixture extracted with methylenechloride. The methylenechloride extract is washed well with water, washed with a sodium hydroxide solution, washed again with water, dried over sodium sulfate and evaporated under reduced pressure to leave a residue of 17β,19-dihydroxy-17α-methyl-5α-androstan-3-one 3-ethylenethioketal which is crystallized once from a solution of acetone-hexane.

Workup

  1. additionthe solution is poured onto water
  2. extractionthe mixture extracted with methylenechloride
  3. extractionThe methylenechloride extract
  4. washis washed well with water
  5. washwashed with a sodium hydroxide solution
  6. washwashed again with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9550a47e5b6f4ebb98458db82a0b267b
Source dataset
uspto-grants-1978_01
Patent number
US04071625

Reaction notes

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