HCID 22633672, compound → HCID 22633670, compound

HRID 2416989Notes

Reaction equation

HRID 2416989 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH3:17])([CH3:16])[CH2:11][CH:10]1[C:5]2=[CH:6][C:7](=[O:18])[CH2:8][CH2:9]1>[Pd](Cl)Cl.[Pd].C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH3:16])([CH3:17])[CH2:11][C:10]1[CH:9]=[CH:8][C:7]([OH:18])=[CH:6][C:5]2=1

Participants

5

Reactant 1

HCID 22633672HCID 22633672, compound

Product 1

HCID 22633670HCID 22633670, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24290Palladium ChlorideCatalystHCID 6386tert-ButanolSolvent

Procedure

6-Bromo-9,9-dimethyl-3-oxo-1,2,3,9,10,10a-hexahydrophenanthrene (0.250 g, 0.819 mmol)), palladium(II) dichloride (0.190 g, 10.7 mmol) and tert-butanol (5 ml) were mixed in a sealed tube and heater to 125-135° C. for 4 hours. The reaction is finished when all the palladium has precipitated on the glass wall and a yellow and transparent reaction mixture is observed. Water was then added and the aqueous phase was extracted with ethyl acetate. The organic extracts were dried with anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (ethyl acetate/hexane 5:95 to 10:90) to give the title material (0.225 g, 91%).

Workup

  1. customhas precipitated on the glass wall
  2. additionWater was then added
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe organic extracts were dried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane 5:95 to 10:90)

Sources & evidence

ORD record
ord-f102f6240a4b4a7591c51db48b6e4c1b
Source dataset
uspto-grants-2004_11
Patent number
US06825233B2

Reaction notes

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