HCID 69736872, compound → HCID 69737255, compound

HRID 967722Notes

Reaction equation

HRID 967722 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:24][C@@:22]2([CH3:23])[C@@H:18]([CH2:19][CH2:20][C:21]2=[O:25])[C@H:17]2[C:8]1=[C:9]1[C:14]([CH2:15][CH2:16]2)=[CH:13][C:12](=[O:26])[CH2:11][CH2:10]1>C(O)C.[Pd]>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH:7]1[CH2:24][C@@:22]2([CH3:23])[C@@H:18]([CH2:19][CH2:20][C:21]2=[O:25])[C@H:17]2[C@H:8]1[C:9]1[CH:10]=[CH:11][C:12]([OH:26])=[CH:13][C:14]=1[CH2:15][CH2:16]2

Participants

4

Reactant 1

HCID 69736872HCID 69736872, compound

Product 1

HCID 69737255HCID 69737255, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6 g of 11-(5-chloropentyl)-estra-4,9-diene-3,17-dione in 100 ml of ethanol is mixed at room temperature with 1 g of palladium on carbon and refluxed under a hydrogen atmosphere for 0.5 hour. Then, the catalyst is filtered off, it is evaporated to the dry state in a vacuum and chromatographed on silica gel with hexane/acetone. 6.2 g of 11-(5-chloropentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one is obtained.

Workup

  1. temperaturerefluxed under a hydrogen atmosphere for 0.5 hour
  2. filtrationThen, the catalyst is filtered off
  3. customit is evaporated to the dry state in a vacuum
  4. customchromatographed on silica gel with hexane/acetone

Sources & evidence

ORD record
ord-ef3c35ecde664001b8831c6c506c97b1
Source dataset
uspto-grants-2005_10
Patent number
US06956031B2

Reaction notes

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