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

HRID 1386571Notes

Reaction equation

HRID 1386571 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-5280e33ae0604b8eae60aa32e05eeae8
Source dataset
uspto-grants-2001_07
Patent number
US06265512B1

Reaction notes

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