Sodium Hydroxide → HCID 88626450, compound

HRID 1193465Notes

Reaction equation

HRID 1193465 reaction equation
[CH2:1]1[C@@H:3]2[C:4](=[O:22])[CH:5]=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3.[OH-:23].[Na+]>>[CH2:1]1[C@@H:3]2[C:4](=[O:22])[CH:5]3[O:23][C:6]43[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH:8]=[CH:7]4

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 13564890HCID 13564890, compound

Product 1

HCID 88626450HCID 88626450, compoundYield 85%

Procedure

To a cooled solution of 1,2β-methylenandrosta-4,6-diene-3,17-dione (2.964 g, 10 mmol) in 120 ml methanol ice cold 36% H2O2 (10 ml) and 2% NaOH (5 ml) is added gradually under stirring and then the mixture allowed to stand at 0°-5° C. for about 20 hours. Then the reaction mixture is poured onto ice, the raw product filtered off, washed with water, dried and purified by column chromatography on silica gel, using CHCl3 as eluant. Thus 2.655 g (85%) of pure title compound is obtained.

Workup

  1. additionThen the reaction mixture is poured onto ice
  2. filtrationthe raw product filtered off
  3. washwashed with water
  4. customdried
  5. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d7141619c9144069840a4978b676e951
Source dataset
uspto-grants-1989_03
Patent number
US04810423

Reaction notes

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