Sodium Acetate → 3,3-Ethylenedioxy-1-methyl-5alpha-androstan-17-one

HRID 67051Notes

Reaction equation

HRID 67051 reaction equation
[CH2:1]1[CH2:25][O:24][C:3]2([CH2:20][C@H:19]([CH3:21])[C@@:18]3([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C@@H:12]3[OH:23])[CH2:4]2)[O:2]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+]>ClCCl.CCOCC>[CH2:25]1[CH2:1][O:2][C:3]2([CH2:20][CH:19]([CH3:21])[C@@:18]3([CH3:22])[C@@H:5]([CH2:6][CH2:7][C@@H:8]4[C@@H:17]3[CH2:16][CH2:15][C@@:13]3([CH3:14])[C@H:9]4[CH2:10][CH2:11][C:12]3=[O:23])[CH2:4]2)[O:24]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 13020861HCID 13020861, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 703602643,3-Ethylenedioxy-1-methyl-5alpha-androstan-17-oneYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

23 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol is agitated for 1 hour at room temperature in 230 ml of dichloromethane with 20 g of pyridinium chlorochromate in the presence of 20 g of sodium acetate. The reaction solution is then diluted with ether, filtered off from the insoluble proportions, and the filtrate is washed with water. After drying and evaporation, 21.5 g of 3,3-ethylenedioxy-1-methyl-5α-androstan-17-one is obtained as the crude product.

Workup

  1. filtrationfiltered off from the insoluble proportions
  2. washthe filtrate is washed with water
  3. customAfter drying
  4. customevaporation

Sources & evidence

ORD record
ord-20e6132d08ec404db949486005c258bd
Source dataset
uspto-grants-1982_08
Patent number
US04344941

Reaction notes

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