Water → 1alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehyde

HRID 1587604Notes

Reaction equation

HRID 1587604 reaction equation
C([O:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([CH:19]=[O:20])[CH3:18])[CH2:8][C@@H:7]([O:28]C(=O)C)[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[OH:4][C@@H:5]1[C@@:25]2([CH3:26])[C:9](=[CH:10][CH:11]=[C:12]3[C@@H:24]2[CH2:23][CH2:22][C@@:21]2([CH3:27])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[CH:17]([CH:19]=[O:20])[CH3:18])[CH2:8][C@@H:7]([OH:28])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 543796531alpha,3beta-Diacetoxypregna-5,7-diene-20-carbaldehyde

Product 1

HCID 538927811alpha,3beta-Dihydroxypregna-5,7-diene-20-carbaldehydeYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

IN 2 ml of methanol was dissolved 73 mg of 1α,3β-diacetoxypregna-5,7-diene-20-carbaldehyde, followed by addition of 5 mg of potassium carbonate. The mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water and extracted with diethyl ether, and the extract was washed with aqueous sodium chloride solution, dried over sodium sulfate and concentrated. The residue was recrystallized from ether to give 49 mg of 1α,3β-dihydroxypregna-5,7-diene-20-carbaldehyde which showed the same 1H NMR spectrum as the 1α,3β-dihydroxypregna-5,7-diene-20-carbaldehyde obtained in Reference Example 2.

Workup

  1. extractionextracted with diethyl ether
  2. washthe extract was washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-0f601c64261f4918ada5ca9e488d6c82
Source dataset
uspto-grants-1993_06
Patent number
US05218109

Reaction notes

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