Perchloric Acid → 6alpha-Chloro-11beta,21-dihydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione

HRID 1577860Notes

Reaction equation

HRID 1577860 reaction equation
C([O:4][CH2:5][C:6](=[O:30])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@H:21]([C@@H:22]([OH:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:27])[CH:17]=[CH:18]2)[C@@H:13]([Cl:28])[CH2:12]3)[CH2:9][C@H:8]1[CH3:29])(=O)C.Cl(O)(=O)(=O)=O>CO>[Cl:28][C@@H:13]1[C:14]2[C@:19]([CH3:20])([CH:18]=[CH:17][C:16](=[O:27])[CH:15]=2)[C@@H:21]2[C@H:11]([C@H:10]3[C@:24]([CH3:25])([CH2:23][C@@H:22]2[OH:26])[C@@H:7]([C:6](=[O:30])[CH2:5][OH:4])[C@H:8]([CH3:29])[CH2:9]3)[CH2:12]1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 7051826521-Acetoxy-6alpha-chloro-11beta-hydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dione

Product 1

HCID 705169726alpha-Chloro-11beta,21-dihydroxy-16alpha-methyl-1,4-pregnadiene-3,20-dioneYield 75.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.5 g of 21-acetoxy-6α-chloro-11β-hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is dissolved in 42 ml of methanol; 1.3 ml of 70% perchloric acid is added thereto and the mixture allowed to stand at room temperature for 20 minutes. The reaction mixture is stirred into ice water, the thus-obtained precipitate is filtered off, washed with water, and dried in the open air. After recrystallization from acetone-diisopropyl ether, 1.02 g of 6α-chloro-11β,21-dihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is obtained, m.p. 128° C. [α]D25 =+55° (chloroform).

Workup

  1. filtrationthe thus-obtained precipitate is filtered off
  2. washwashed with water
  3. customdried in the open air
  4. customAfter recrystallization from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-6f9b851582a44ef6a90e0e12a381dbbe
Source dataset
uspto-grants-1981_09
Patent number
US04289763

Reaction notes

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