Water → HCID 86733324, compound

HRID 1606475Notes

Reaction equation

HRID 1606475 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:10]3[C@H:11]4[C@:18]([CH3:27])([CH2:19][C:20](=[O:26])[C:21]=32)[C@@H:14]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:12]4)[CH2:6]1)(=O)C.Cl(O)(=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:10]3[C@H:11]4[C@:18]([CH3:27])([CH2:19][C:20](=[O:26])[C:21]=32)[C@@H:14]([C:15](=[O:17])[CH3:16])[CH2:13][CH2:12]4)[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 24247Perchloric AcidHCID 86733325HCID 86733325, compound

Product 1

HCID 86733324HCID 86733324, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3α-Acetoxy-5α-pregn-8-ene-11,20-dione (400 mg.) was dissolved in methanol (40 ml.) and perchloric acid (60% w/v; 2 ml.) was added and the solution was allowed to stand at room temperature for 19 hours. The reaction mixture was poured into water and the steroid extracted with chloroform. The solvent was removed from the extract and the residue twice crystallised from methyl acetate-petrol to give the title compound (135 mg.) m.p. 170°-172°, [α]D + 250°.

Workup

  1. extractionthe steroid extracted with chloroform
  2. customThe solvent was removed from the
  3. extractionextract
  4. customthe residue twice crystallised from methyl acetate-petrol

Sources & evidence

ORD record
ord-acce805e65574d84a306a9306ec4e987
Source dataset
uspto-grants-1976_04
Patent number
US03953429

Reaction notes

Loading…