Hydrogen Peroxide → HCID 86733178, compound

HRID 268197Notes

Reaction equation

HRID 268197 reaction equation
C([O:4][C@@H:5]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[CH:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:26])[CH2:19][C@@:18]2([CH3:27])[C@H:11]3[CH2:12][C:13]([CH3:28])=[C:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.[OH:29]O.[OH-]>CO>[O:29]1[C@:14]2([C@:18]3([CH3:27])[C@@H:11]([CH2:12][C@@:13]12[CH3:28])[C@H:10]1[C@@H:21]([C@:22]2([CH3:25])[CH:7]([CH2:8][CH2:9]1)[CH2:6][C@H:5]([OH:4])[CH2:24][CH2:23]2)[C:20](=[O:26])[CH2:19]3)[C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 961HydroxideHCID 54314275HCID 54314275, compound

Product 1

HCID 86733178HCID 86733178, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 20.0 g. of 3α-acetoxy-16-methyl-16-pregnene-11,20-dione dissolved in 600 ml. of methanol, is cooled to 18°C., and 80 ml. of 30% hydrogen peroxide followed by 80 ml. of 2.5 N sodiim hydroxide are added. Considerable material precipitates from solution, but all redissolves on stirring the reaction mixture at 25°-30°C. for 40 minutes. The solution is kept at 15°-20°C. for 18 hours at which time the ultraviolet maximum at 249 has completely disappeared. Then 600 ml. of saturated salt water is slowly added, the crystalline precipitate is filtered, washed with water, and dried in air and in vacuum. The 16α,17α-epoxy-3α-hydroxy-16β-methyl-pregnane-11,20-dione thus formed weighs about 17 g.

Workup

  1. customConsiderable material precipitates from solution
  2. dissolutionall redissolves
  3. waitThe solution is kept at 15°-20°C. for 18 hours at which time
  4. additionof saturated salt water is slowly added
  5. filtrationthe crystalline precipitate is filtered
  6. washwashed with water
  7. customdried in air and in vacuum

Sources & evidence

ORD record
ord-9671d43925db42a6b8388760797b2a66
Source dataset
uspto-grants-1976_03
Patent number
US03947409

Reaction notes

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