p-Toluenesulfonic acid → 1alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehyde

HRID 1196328Notes

Reaction equation

HRID 1196328 reaction equation
CC1(C)CO[CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([OH:30])[CH2:20][C@@H:21]3[OH:29])=[CH:16][CH:15]=4)[CH2:12][CH2:11]2)[CH3:9])[O:4]C1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>CC(C)=O>[OH:29][C@@H:21]1[C@@:22]2([CH3:23])[C:17](=[CH:16][CH:15]=[C:14]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:13]3[CH2:12][CH2:11][C@@H:10]2[CH:8]([CH:5]=[O:4])[CH3:9])[CH2:18][C@@H:19]([OH:30])[CH2:20]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 21226206Ethyl acetate hexaneHCID 6785294520-(5,5-Dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1alpha,3beta-diol

Product 1

HCID 538927811alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In 10 ml of acetone was dissolved 4.3 mg (0.010 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)pregna-5,7-diene-1α,3β-diol, followed by addition of 1 ml of a 1 mmole/l solution of p-toluenesulfonic acid in acetone (containing 0.001 mmole of p-toluenesulfonic acid). The mixture was refluxed for 2 hours. The reaction mixture thus obtained was cooled to room temperature and the solvent was distilled off under reduced pressure. The residue was dissolved in 40 ml of methylene chloride and this methylene chloride solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in that order and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:5, v/v) to give 2.8 mg of 1α,3β-dihydroxypregna-5,7-diene-20-carbaldehyde (yield: 82%).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe reaction mixture thus obtained
  3. distillationthe solvent was distilled off under reduced pressure
  4. dissolutionThe residue was dissolved in 40 ml of methylene chloride
  5. washthis methylene chloride solution was washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution in that order
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-739f9e4c4ae446e880c719ded225d5d5
Source dataset
uspto-grants-1992_05
Patent number
US05112998

Reaction notes

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