Hydrogen Peroxide → HCID 23631321, compound

HRID 1659840Notes

Reaction equation

HRID 1659840 reaction equation
[CH2:1]1[CH2:10][O:9][CH:8]2[CH:3]([C@:4]3([CH2:23][CH2:22][C@H:21]4[C@@H:11]([CH:12]=[CH:13][C:14]5[C@:19]4([CH3:20])[CH:18]=[CH:17][C:16](=[O:24])[CH:15]=5)[C@@H:6]3[CH2:7]2)[CH3:5])[O:2]1.[OH-:25].[Na+].OO.O>CO>[CH2:1]1[CH2:10][O:9][C:3]2([CH2:8][CH2:7][C@H:6]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:4]23[CH3:5])[C@:19]2([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[C@@H:17]3[O:25][C@@H:18]32)[CH:13]=[CH:12]4)[O:2]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 131712611HCID 131712611, compound

Product 1

HCID 23631321HCID 23631321, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.0 g of 17, 17-ethylenedioxy-androsta-1,4,6-trien-3-one in 40 ml of methanol is treated at room temperature with 0.28 ml of 10% methanolic sodium hydroxide and 1.8 ml of 30% hydrogen peroxide and stirred at room temperature for 4.5 hours. 50 ml of water are added dropwise to the solution, the separated product is collected by suction and chromatographed on 30 g of silica gel. Elution with hexane/ether (3:2) yields 0.793 g (75%) of crystalline 17,17-ethylenedioxy-1α,2α-epoxy-androsta-4,6-dien-3-one. The analytical sample is prepared by recrystallisation from ether; melting point 181°-186° C.; [α]D25 =+167° (c=0.5 in dioxan); UV (ethanol): λmax 291 nm (ε=19270).

Workup

  1. customthe separated product is collected by suction
  2. customchromatographed on 30 g of silica gel
  3. washElution with hexane/ether (3:2)

Sources & evidence

ORD record
ord-a6e6fdfc7bd84d2383b7a4e95ce14a4f
Source dataset
uspto-grants-1981_12
Patent number
US04305881

Reaction notes

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