Sulfuric Acid → 1alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylic acid

HRID 1587610Notes

Reaction equation

HRID 1587610 reaction equation
[CH3:1][O:2][C:3]([O:5][C@@H:6]1[C@@:26]2([CH3:27])[C:10](=[CH:11][CH:12]=[C:13]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[CH:18]([CH:20]=[O:21])[CH3:19])[CH2:9][C@@H:8]([O:29][C:30]([O:32][CH3:33])=[O:31])[CH2:7]1)=[O:4].CC(C)=[O:36].OS(O)(=O)=O.O=[Cr](=O)=O.[Cr](O)(O)(=O)=O.S(=O)(=O)(O)O>CC(C)=O.O.C(O)(C)C>[CH3:1][O:2][C:3]([O:5][C@@H:6]1[C@@:26]2([CH3:27])[C:10](=[CH:11][CH:12]=[C:13]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:14]3[CH2:15][CH2:16][C@@H:17]2[CH:18]([C:20]([OH:36])=[O:21])[CH3:19])[CH2:9][C@@H:8]([O:29][C:30]([O:32][CH3:33])=[O:31])[CH2:7]1)=[O:4]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 24425Chromic AcidHCID 543675231alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehydeHCID 131709961Jones' reagent

Product 1

HCID 537642171alpha,3beta-Bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylic acid

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

In 5 ml of acetone was dissolved 120 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carbaldehyde and the solution was stirred with ice-cooling. Then, Jones' reagent prepared by mixing chromic acid with concentrated sulfuric acid and diluting the mixture with water in accordance with the method of K. Bowden et al. (J. Chem. Soc., p. 39, (1946)) was added dropwise to the above solution until the red color of the reagent would be persistent. After the excess reagent was decomposed with isopropyl alcohol, the reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulfate and concentrated to give 85 mg of 1α,3β-bis(methoxycarbonyloxy)pregna-5,7-diene-20-carboxylic acid.

Workup

  1. temperaturecooling
  2. additionBowden et al. (J. Chem. Soc., p. 39, (1946)) was added dropwise to the above solution until the red color of the reagent
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. additionThe residue was diluted with water
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7f0f9bf1b9204e50949a619266b26913
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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