Diethyl Ether → 3,3-Ethylenedioxy-1alpha-methyl-5alpha-androstan-17-one

HRID 262966Notes

Reaction equation

HRID 262966 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.[Al].CCOCC>C1(C)C=CC=CC=1.C1(=O)CCCCC1>[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 3283Diethyl EtherHCID 5359268AluminumHCID 13020861HCID 13020861, compound

Product 1

HCID 130208633,3-Ethylenedioxy-1alpha-methyl-5alpha-androstan-17-oneYield 93.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 7967CyclohexanoneSolvent

Procedure

55 g of 3,3-ethylenedioxy-17β-hydroxy-1α-methyl-5α-androstane in 550 ml of toluene and 110 ml of cyclohexanone were treated at boiling with a solution of 5.5 g of aluminium isopropylate in 55 ml of toluene and the mixture was heated for 3 hours with slow distillation. The mixture was then treated with ether, washed with ice-cold dilute sulphuric acid and water, evaporated and the residue steam-distilled. After extraction with methylene chloride, the resulting product was recrystallised from diisopropyl ether to give 51 g of 3,3-ethylenedioxy-1α-methyl-5α-androstan-17-one of melting point 155.5°-156.6° C.

Workup

  1. temperaturethe mixture was heated for 3 hours with slow distillation
  2. washwashed with ice-cold dilute sulphuric acid and water
  3. customevaporated
  4. distillationthe residue steam-distilled
  5. extractionAfter extraction with methylene chloride
  6. customthe resulting product was recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-559e5ff3053b4fc98d557938fcdf9b1e
Source dataset
uspto-grants-1979_05
Patent number
US04155918

Reaction notes

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