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

HRID 2302024Notes

Reaction equation

HRID 2302024 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-b0c37ebeddcc4a03a629694766f83dd3
Source dataset
uspto-grants-2002_08
Patent number
US06429274B1

Reaction notes

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