Sodium Hydroxide → HCID 70626625, compound

HRID 616350Notes

Reaction equation

HRID 616350 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[OH-].[Na+].[F:9][C@H:10]1[CH2:29][C@@:28]2([CH3:30])[C@@H:21]([CH2:22][CH2:23][C@:24]2([OH:31])[C:25](=[O:27])[CH3:26])[C@H:20]2[C@H:11]1[C@:12]1([CH3:33])[C:17]([CH:18]=[CH:19]2)=[CH:16][C:15](=[O:32])[CH:14]=[CH:13]1>CS(C)=O>[F:9][C@H:10]1[CH2:29][C@@:28]2([CH3:30])[C@@H:21]([CH2:22][CH2:23][C@:24]2([OH:31])[C:25](=[O:27])[CH3:26])[C@H:20]2[C@H:11]1[C@:12]1([CH3:33])[C:17]([CH:18]=[CH:19]2)=[CH:16][C:15](=[O:32])[C@@H:14]2[CH2:2][C@H:13]12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 54357567HCID 54357567, compound

Product 1

HCID 70626625HCID 70626625, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

One gram of trimethylsulfoxonium iodide in 30 ml. of dimethyl sulfoxide is agitated under nitrogen for 30 minutes with 200 mg. of pulverized sodium hydroxide. Then, 1.6 g. of 11β-fluoro-17-hydroxy-1,4,6-pregnatriene-3,20-dione is added to the reaction mixture. After 4.5 hours, the reaction mixture is stirred into acetic ice/water. The precipitate is vacuum-filtered, taken up in methylene chloride, and dried over sodium sulfate. After chromatographing the crude product on silica gel with acetone/hexane, 1.4 g. of 11β-fluoro-17-hydroxy-1α,2α -methylene-4,6-pregnadiene-3,20-dione is obtained. UV: ε282 = 16,900.

Workup

  1. filtrationThe precipitate is vacuum-filtered
  2. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-b45888a0ae9d4928aed15d3e7246bbf0
Source dataset
uspto-grants-1978_02
Patent number
US04073900

Reaction notes

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