Perchloric Acid → HCID 70519079, compound

HRID 1577863Notes

Reaction equation

HRID 1577863 reaction equation
C([O:4][CH2:5][C:6](=[O:31])[C@@H:7]1[C@:24]2([CH3:25])[C@H:10]([C@H:11]3[C@:21]([Cl:27])([C@@H:22]([OH:26])[CH2:23]2)[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:28])[CH:17]=[CH:18]2)[C@@H:13]([Cl:29])[CH2:12]3)[CH2:9][C@H:8]1[CH3:30])(=O)C.Cl(O)(=O)(=O)=O>CO>[Cl:29][C@@H:13]1[C:14]2[C@:19]([CH3:20])([CH:18]=[CH:17][C:16](=[O:28])[CH:15]=2)[C@:21]2([Cl:27])[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:31])[CH2:5][OH:4])[C@H:8]([CH3:30])[CH2:9]3)[CH2:12]1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 70518226HCID 70518226, compound

Product 1

HCID 70519079HCID 70519079, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.90 g of 21-acetoxy-6α,9-dichloro-11β-hydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is dissolved in 53 ml of methanol. The mixture is conbined with 1.7 ml of 70% perchloric acid and allowed to stand for 20 hours at room temperature. The reaction mixture is poured into ice water; the precipitated product is isolated and chromatographed on silica gel. With 37-52% ethyl acetate-dichloromethane, after recrystallization from acetone-diisopropyl ether, 807 mg of 6α,9-dichloro-11β,21-dihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is obtained, m.p. 230° C. [α]D25 =+99° (chloroform).

Workup

  1. customthe precipitated product is isolated
  2. customchromatographed on silica gel
  3. customWith 37-52% ethyl acetate-dichloromethane, after recrystallization from acetone-diisopropyl ether

Sources & evidence

ORD record
ord-e7ba8bb4ff9c4aa7962684d286cd21ec
Source dataset
uspto-grants-1981_09
Patent number
US04289763

Reaction notes

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