p-Toluenesulfonic acid → 1alpha,2alpha-Epoxy-3beta,7alpha-dihydroxypregn-5-ene-20-carbaldehyde

HRID 1708769Notes

Reaction equation

HRID 1708769 reaction equation
CC1(C)CO[CH:5]([CH:8]([C@@H:10]2[C@:27]3([CH3:28])[C@H:13]([C@H:14]4[C@H:24]([CH2:25][CH2:26]3)[C@:22]3([CH3:23])[C:17]([CH2:18][C@@H:19]([OH:30])[C@@H:20]5[O:29][C@@H:21]53)=[CH:16][C@H:15]4[OH:31])[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>[O:29]1[C@H:20]2[C@H:19]([OH:30])[CH2:18][C:17]3[C@:22]([CH3:23])([C@@H:21]12)[C@@H:24]1[C@H:14]([C@H:13]2[C@:27]([CH3:28])([CH2:26][CH2:25]1)[C@@H:10]([CH:8]([CH:5]=[O:4])[CH3:9])[CH2:11][CH2:12]2)[C@H:15]([OH:31])[CH:16]=3

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 21226206Ethyl acetate hexaneHCID 8674580820-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxypregn-5-ene-3beta,7alpha-diol

Product 1

HCID 867458101alpha,2alpha-Epoxy-3beta,7alpha-dihydroxypregn-5-ene-20-carbaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

In 2.5 ml of acetone was dissolved 2.2 mg (0.005 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxypregn-5-ene-3β,7α-diol, followed by addition of 0.5 ml of a 1 mmol/1 solution of p-toluenesulfonic acid in acetone (containing 0.0005 mmole of p-toluenesulfonic acid). The mixture was stirred at room temperature for 12 hours. From the reaction mixture thus obtained, the solvent was distilled off under reduced pressure and methylene chloride was added to the residue. This methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by silica gel chromatography (eluent:ethyl acetate-hexane=1:5, v/v) to recover 1.2 mg of 1α,2α-epoxy- 3β,7α-dihydroxypregna-5-ene-20-carbaldehyde (yield: 67%).

Workup

  1. customFrom the reaction mixture thus obtained
  2. distillationthe solvent was distilled off under reduced pressure and methylene chloride
  3. additionwas added to the residue
  4. washThis methylene chloride solution was washed successively with saturated aqueous sodium hydrogen carbonate and saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-1049bcfd56ee4c5ea2275c3937024b76
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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