Fluorene → HCID 129845837, compound

HRID 483475Notes

Reaction equation

HRID 483475 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]([CH3:21])=[C:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1>C1COCC1>[CH:16]1([C:15]([C:1]2[C:13]3[CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:4]=[CH:3][CH:2]=2)([CH3:21])[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17]1

Participants

4

Reactant 2

HCID 6853FluoreneHCID 1374671,3-Cyclopentadiene, 5-(1-methylethylidene)-

Product 1

HCID 129845837HCID 129845837, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 200 ml of THF and 16.5 g of fluorene cooled to a temperature of -50° C. or lower in a 500-ml flask thoroughly purged with nitrogen was added 67 ml of a dil. methyllithium diethyl ether solution (1.4 M) dropwise over 30 minutes. The mixture was warmed gradually to room temperature and subjected to reaction for 3 hours. The reaction mixture was cooled back to a temperature of -50° C. or lower and 10 g of 6,6-dimethylfulvene was added dropwise over 30 minutes. After the addition was completed, the solution was warmed slowly to room temperature and subjected to reaction for 2 days. The reaction was terminated by the addition of 60 ml of H2O, and the ether layer was separated and dehydrated over anhydrous MgSO4. Drying ether by evaporation, gave 17.6 g of 2-cyclopentadienyl-2-fluorenylpropane as crude crystals.

Workup

  1. customthoroughly purged with nitrogen
  2. additionwas added 67 ml of a dil. methyllithium diethyl ether solution (1.4 M) dropwise over 30 minutes
  3. customsubjected to reaction for 3 hours
  4. temperatureThe reaction mixture was cooled back to a temperature of -50° C.
  5. additionAfter the addition
  6. temperaturethe solution was warmed slowly to room temperature
  7. customsubjected to reaction for 2 days
  8. customThe reaction was terminated by the addition of 60 ml of H2O
  9. customthe ether layer was separated
  10. customDrying ether by evaporation

Sources & evidence

ORD record
ord-85388c2674a34fdfa6b5689de3b6eb55
Source dataset
uspto-grants-1993_07
Patent number
US05225501

Reaction notes

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