Acetone → 6alpha,7alpha-Diepoxypregn-4-ene-20-carbaldehyde

HRID 1708765Notes

Reaction equation

HRID 1708765 reaction equation
C(O[C@H:5]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[C:7]3[C@:8]4([O:27][C:6]1=3)[O:26][C@H:9]4[C@@H:10]1[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:25])[C@H:11]1[CH2:12][CH2:13][C@@H:14]2[CH2:15][CH3:16])(=O)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C[C:46](C)=[O:47]>>[O:27]1[C:6]2=[C:7]3[C@:21]([CH3:24])([CH2:22][CH2:23][CH2:5]2)[C@@H:20]2[C@H:10]([C@H:11]4[C@:17]([CH3:25])([CH2:18][CH2:19]2)[C@@H:14]([CH:15]([CH:46]=[O:47])[CH3:16])[CH2:13][CH2:12]4)[C@@H:9]2[O:26][C@:8]123

Participants

4

Reactant 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 867458006alpha,7alpha-Diepoxypregn-4-en-3beta-yl acetate

Product 1

HCID 867458076alpha,7alpha-Diepoxypregn-4-ene-20-carbaldehydeYield 48%

Procedure

In 5 ml of acetone was dissolved 24.3 mg (0.05 mmole ) of 20-(5,5-dimethyl-1,3 -dioxan-2-yl)-1α,2α;6α,7α-diepoxypregn-4-en-3β-yl acetate, followed by addition of 2.5 mg (0.01 mmole) of pyridinium p-toluenesulfonate. 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. To the residue was added methylene chloride and the mixture was washed successively with saturated aqueous sodium hydrogen carbonate solution 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 9.6 mg of 3β-acetoxy-1α,2α;6α,7α-diepoxypregn-4-ene-20-carbaldehyde (yield: 48%).

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. additionTo the residue was added methylene chloride
  5. washthe mixture was washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was then distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (eluent
  9. customethyl acetate-hexane=1:5, v/v) to recover 9.6 mg of 3β-acetoxy-1α,2α

Sources & evidence

ORD record
ord-a70018f7543b4c85932159371175b0af
Source dataset
uspto-grants-1994_10
Patent number
US05359055

Reaction notes

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