1H-Cyclopenta[l]phenanthrene → 1H-Cyclopenta[l]phenanthrene, 2,3-dihydro-

HRID 1279672Notes

Reaction equation

HRID 1279672 reaction equation
[CH2:1]1[C:5]2[C:6]3[C:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:4]=2[CH:3]=[CH:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[H][H]>[Pd].C1(C)C=CC=CC=1>[CH2:3]1[C:4]2[C:17]3[C:12]([C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]=2[CH2:1][CH2:2]1)=[CH:13][CH:14]=[CH:15][CH:16]=3

Participants

5

Reactant 2

HCID 118061071H-Cyclopenta[l]phenanthreneHCID 178418361HCID 178418361, compound

Product 1

HCID 6128121H-Cyclopenta[l]phenanthrene, 2,3-dihydro-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2 g cyclopentaphenanthrene, 0.2 g 10% palladium on carbon and 50 mL toluene was stirred under hydrogen (69 kPa) until hydrogen uptake ceased, about 48 h. Catalyst was removed by filtration through diatomaceous earth and the filtrate evaporated. The crude product remaining weighed 1.97 g. It was further purified by recrystallization from heptane at −40° C. to give 1.8 g colorless plates. Spectroscopic and chemical analysis confirmed the identity of the desired compound.

Workup

  1. customCatalyst was removed by filtration through diatomaceous earth
  2. customthe filtrate evaporated
  3. customIt was further purified by recrystallization from heptane at −40° C.
  4. customto give 1.8 g colorless plates

Sources & evidence

ORD record
ord-19e147d26f284bde827d5b5af2a3eb28
Source dataset
uspto-grants-2002_09
Patent number
US06448358B2

Reaction notes

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