p-Toluenesulfonic acid → HCID 56615254, compound

HRID 652216Notes

Reaction equation

HRID 652216 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.C1CO[C:14]2([CH:19]=[CH:18][C@H:17]3[C@H:20]4[C@H:30]([C@@H:31]([OH:33])[CH2:32][C@:15]23[CH3:16])[C@:28]2([CH3:29])[C:23]([CH2:24][C@@H:25]([OH:34])[CH2:26][CH2:27]2)=[CH:22][CH2:21]4)[O:13]1>O.CC(C)=O>[OH:34][C@H:25]1[CH2:26][CH2:27][C@@:28]2([CH3:29])[C:23](=[CH:22][CH2:21][C@@H:20]3[C@@H:30]2[C@@H:31]([OH:33])[CH2:32][C@@:15]2([CH3:16])[C@H:17]3[CH:18]=[CH:19][C:14]2=[O:13])[CH2:24]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 56609748HCID 56609748, compound

Product 1

HCID 56615254HCID 56615254, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4 ml of a solution of 100 mg of p-toluenesulphonic acid in 10 ml of water are added to a solution of 800 mg of 17,17-ethylenedioxyandrosta-5,15-diene-3β,11β-diol in 40 ml of acetone and the whole is stirred for 6 hours at room temperature. After dilution with 40 ml of water, the acetone is distilled off under a water-jet vacuum and the oily residue is taken up in chloroform and washed with ice-cold saturated sodium bicarbonate solution. Evaporation of the organic solvent yields amorphous 3β,11β-dihydroxyandrosta-5,15-dien-17-one which can be used for the next step without further purification.

Workup

  1. distillationAfter dilution with 40 ml of water, the acetone is distilled off under a water-jet vacuum
  2. washwashed with ice-cold saturated sodium bicarbonate solution
  3. customEvaporation of the organic solvent

Sources & evidence

ORD record
ord-d792930241034b37b36aec96850cce23
Source dataset
uspto-grants-1987_06
Patent number
US04670551

Reaction notes

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