Methylenephenanthrene → 8,9-Dihydrocyclopenta[def]phenanthrene

HRID 1172018

Reaction equation

HRID 1172018 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>[Pd].CCO>[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

4

Reactant 1

HCID 9147Methylenephenanthrene

Product 1

HCID 6057498,9-Dihydrocyclopenta[def]phenanthreneYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4H-cyclopenta[def]phenanthrene (4.75 g, 25 mmol) was put into a Par reactor bottle, and EtOH (200 ml) was added thereto. 5% Pd/C (3.99 g) was added to the reaction solution, and the resultant solution was incubated under a hydrogen pressure of 40 psi for 24 hours. After the reaction was terminated, the reaction solution was filtered, and the filtrate was concentrated under a reduced pressure to give a white product (4.32 g, 90%).

Workup

  1. additionwas added
  2. customfor 24 hours
  3. customAfter the reaction was terminated
  4. filtrationthe reaction solution was filtered
  5. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-8864606e6b8144138958006221ce1ef8
Source dataset
uspto-grants-2010_11
Patent number
US07833635B2

Linked notes

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