Potassium Hydroxide → 11alpha-Hydroxy-7alpha-methylestr-4-ene-3,17-dione

HRID 900680Notes

Reaction equation

HRID 900680 reaction equation
C([O:4][C@@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:23])[C@H:15]2[C@H:6]1[C@@H:7]1[C:12]([CH2:13][C@H:14]2[CH3:24])=[CH:11][C:10](=[O:25])[CH2:9][CH2:8]1)(=O)C.[OH-].[K+]>O>[OH:4][C@@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2=[O:23])[C@H:15]2[C@H:6]1[C@@H:7]1[C:12]([CH2:13][C@H:14]2[CH3:24])=[CH:11][C:10](=[O:25])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12020272HCID 12020272, compound

Product 1

HCID 1202027311alpha-Hydroxy-7alpha-methylestr-4-ene-3,17-dioneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1 g of 11α-acetoxy-7α-methyl-estr-4-ene-3,17-dione (E) in 20 ml of a 0.2 molar methanolic potassium hydroxide solution was stirred at room temperature for 3 hours. Then, it was added to water, extracted three times with ethyl acetate, washed neutral, dried on sodium sulfate, concentrated by evaporation in a vacuum and recrystallized from diethyl ether/acetone. 878 mg of pure 11α-hydroxy-7α-methyl-estr-4-ene-3,17-dione (F) with a melting point of 202.3° C. was obtained ([α]D20=+44.8° (c=0.5% in chloroform)).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed neutral
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customrecrystallized from diethyl ether/acetone

Sources & evidence

ORD record
ord-304238a8c7024069bcddd78f47275836
Source dataset
uspto-grants-2008_04
Patent number
US07361645B2

Reaction notes

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