Perchloric Acid → Allopregnanolone

HRID 232797

Reaction equation

HRID 232797 reaction equation
C([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.Cl(O)(=O)(=O)=O>CO>[OH:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 53835422Allopregnan-3alpha-ol-20-one acetate

Product 1

HCID 92786AllopregnanoloneYield 107.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3α-acetoxy-5α-pregnan-20-one (4.8 g) in 150 mL of methanol was cooled to 0° C. with an ice bath and 15.0 mL of perchloric acid was added dropwise. After 30 m of stirring, the ice bath was removed and the reaction mixture was left stirring for three days. The reaction mixture was poured into water and extracted with chloroform three times. The chloroform extracts were combined, dried over magnesium sulfate, and the solvent evaporated to give 4.57 g of crude product.

Workup

  1. customthe ice bath was removed
  2. waitthe reaction mixture was left
  3. stirringstirring for three days
  4. additionThe reaction mixture was poured into water
  5. extractionextracted with chloroform three times
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-d869891b434249c19eacca768a8e4da3
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Linked notes

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