Hydrogen Peroxide → HCID 86734050, compound

HRID 1287368Notes

Reaction equation

HRID 1287368 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:21])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:23])[CH2:4][CH2:5][C:6](=[O:22])[CH:7]=1.[OH:24]O.[OH-].[Na+]>CO.O.ClCCl>[O:24]1[C:8]23[C@:3]([CH3:23])([CH2:4][CH2:5][C:6](=[O:22])[C@H:7]12)[C@:2]1([F:1])[C@H:11]([C@H:12]2[C@@:16]([CH2:18][C@@H:19]1[OH:20])([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]2)[CH2:10][CH2:9]3

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 23616821357-09-5

Product 1

HCID 86734050HCID 86734050, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 10g of 9-fluoro-11β-hydroxyandrost-4-ene-3,17-dione in 1.5 liter of methanol is stirred at room temperature with 30ml of 30% hydrogen peroxide and 20ml of 4N sodium hydroxide solution. The resulting solution is diluted with 4 liters of water and extracted with dichloromethane. The dichloromethane solution is washed with 5% hydrochloric acid, 5% sodium bicarbonate solution, water, dried, and evaporated in vacuo to give 9.1g of crude product. This material is dissolved in dichloromethane and chromatographed on a 100g-silica gel column. Elution with the same solvent gives 3.39g of the title compound and some impure material which is rechromatographed to give a further 1.71g of the title compound.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane solution is washed with 5% hydrochloric acid, 5% sodium bicarbonate solution, water
  3. customdried
  4. customevaporated in vacuo
  5. customto give 9.1g of crude product
  6. customchromatographed on a 100g-silica gel column
  7. washElution with the same solvent

Sources & evidence

ORD record
ord-bf10ed2a08ef4272b0a9eebb01ee4cc4
Source dataset
uspto-grants-1976_10
Patent number
US03984474

Reaction notes

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