Methylenephenanthrene → 8,9-Dihydrocyclopenta[def]phenanthrene

HRID 2205266Notes

Reaction equation

HRID 2205266 reaction equation
[CH:1]1[C:14]2[C:5]3=[C:6]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH2:15][C:4]3=[CH:3][CH:2]=1.[H][H]>CCO.[Pd]>[CH:10]1[C:11]2[CH2:12][CH2:13][C:14]3[CH:1]=[CH:2][CH:3]=[C:4]4[CH2:15][C:7]([C:6]=2[C:5]=34)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 9147MethylenephenanthreneHCID 178418361HCID 178418361, compound

Product 1

HCID 6057498,9-Dihydrocyclopenta[def]phenanthreneYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10.0 g (52.6 mmol) of 4H-cyclopenta[def]phenanthrene and 8.40 g of 5% Pd/C were dissolved in 70 ml of EtOH in a Par reactor bottle, and the resultant solution was stirred at room temperature for 24 hours with hydrogen pressure being maintained at 40 psi. After the reaction was completed, the reaction solution was filtered and the solvent was evaporated therefrom to obtain 8.60 g of white target material (yield: 85.0%). The obtained compound was confirmed by liquid chromatography-mass spectrometry (LC-MS).

Workup

  1. temperaturebeing maintained at 40 psi
  2. filtrationthe reaction solution was filtered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d8398325906c4fdda96f83f90049659c
Source dataset
uspto-grants-2016_06
Patent number
US09371270B2

Reaction notes

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