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

HRID 279852Notes

Reaction equation

HRID 279852 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](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(OCC)(=O)C>CN(C)C=O.[Cr]>[CH2:25]1[CH2:1][O:2][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:12]3=[O:23])[CH2:4]2)[O:24]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 13020861HCID 13020861, compound

Product 1

HCID 130208633,3-Ethylenedioxy-1alpha-methyl-5alpha-androstan-17-oneYield 100.6%

Reagents, catalysts & solvents 2

HCID 23976ChromiumCatalystHCID 6228DimethylformamideSolvent

Procedure

35 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17β-ol is stirred in 350 ml of dimethylformamide with 70 g of pyridinium dichromate for 17 hours at room temperature. The reaction solution is stirred into ten times the amount of ethyl acetate, then the thus-separated chromium salts are left behind by decanting, and the organic phase is washed with water. After drying and evaporation, 35 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17-one is produced, mp 154° C.

Workup

  1. customby decanting
  2. washthe organic phase is washed with water
  3. customAfter drying
  4. customevaporation

Sources & evidence

ORD record
ord-5b2cce0c8dd749659a28ec4a0d0934b9
Source dataset
uspto-grants-1986_05
Patent number
US04587235

Reaction notes

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